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7 reactions in Reaxys
2018-05-28 07h:53m:02s (UTC)
Cl
N
1. Query HO
Search as: Product, As drawn, No mixtures ))
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2H
2
H
Cl
Cl
2
H
O
N
H 2N
HO
Br
Rx-ID: 28008058 View in Reaxys 1/7 Yield
Conditions & References 2.2 :At about -30° C., (1-Bromocyclopentyl)-(2-chlorophenyl)-methanone (1 g, 3.48 mmol) was treated with liquid methylamine (approx. 2 mL). After about 1 hour, the excess methylamine was evaporated, and the resulting residue was dissolved in hexane and re-evaporated. The residue was dissolved in diethyl ether (10 mL), and hydrochloride gas was pumped in. The resulting precipitate was collected by filtration to give the title product (700 mg, 73percent). 1H NMR (300 MHz, CD3OD) δ 7.76-7.49 (m, 3H), 2.47-1.74 (m, 8H); LC-MS: m/z=241 (MH)+. in water, Time= 1h, T= -30 °C Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/268071; (2008); (A1) English View in Reaxys 2H
2H
2H 2H
2H
2H
Br
2H
O Cl
2H
Cl
2H
N
2H
2H
N
2H
HO
2H
2H
2H
2H
2H
2H
2H
2H 2H
2
H 2H
2H
Rx-ID: 28008061 View in Reaxys 2/7 Yield
Conditions & References 1.3 :The procedure of Step 3 is carried out as described in U.S. Pat. No. 3,254,124. d8-(1-Bromocyclopentyl)-(2-chlorophenyl)methanone (about 30 g) is treated with liquid d8-methylamine (about 50 mL; d5-Methylamine gas is commercially available from Sigma-Aldrich, St. Louis Mo. 63103). After about 1 hour, the excess d5-methylamine is removed in vacuo and the resulting residue is dissolved in pentane. The solvent is removed in vacuo to give the title product. in pentane, Time= 1h Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/268071; (2008); (A1) English View in Reaxys
2H
N OH
2H
2H
2H 2H
2H
Cl
Cl
N HCl HO
Rx-ID: 28008065 View in Reaxys 3/7 Yield
Conditions & References 2.2 :At about -30° C., (1-Bromocyclopentyl)-(2-chlorophenyl)-methanone (1 g, 3.48 mmol) was treated with liquid methylamine (approx. 2 mL). After about 1 hour, the excess methylamine was evaporated, and the resulting residue was dissolved in hexane and re-evaporated. The residue was dissolved in diethyl ether (10 mL), and hydrochloride gas was pumped in. The resulting precipitate was collected by filtration to give the title product (700 mg, 73percent). 1H NMR (300 MHz, CD3OD) δ 7.76-7.49 (m, 3H), 2.47-1.74 (m, 8H); LC-MS: m/z=241 (MH)+. With hydrogenchloride in diethyl ether
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Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/268071; (2008); (A1) English View in Reaxys 2H
2H
2H
2H
Br
2H 2H
O
Cl
2H
Cl
N
2H
2H
2H
2H
H 2N
2
H 2 H
2 2H
HO 2H
2H
H
2H 2H
2H 2H
2H
Rx-ID: 28008067 View in Reaxys 4/7 Yield
Conditions & References 3.3 :At about -30° C., d11-(1-Bromocyclopentyl)-(2-chlorophenyl)-methanone (450 mg, 1.52 mmol) was treated with liquid d3methylamine (about 2 mL). After about 1 hour, the excess methylamine was evaporated, and the resulting residue was dissolved in hexane and re-evaporated. The residue was dissolved in diethyl ether (10 mL), and hydrochloride, gas was pumped in. The resulting precipitate was collected by filtration to give the title product (150 mg, 35percent). 1H NMR (300 MHz, CD3OD) δ 7.76-7.54 (m, 4H); LC-MS: m/z=249 (MH)+. , Time= 1h, T= -30 °C Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/268071; (2008); (A1) English View in Reaxys 2H
2H
Cl
2H 2H
2H
N
2H
OH
2H
2H
N
2H
Cl 2H
2H
HCl
HO 2H
2H 2H
2H
2H
2H
2H
2H
2H 2H
2H
Rx-ID: 28008069 View in Reaxys 5/7 Yield
Conditions & References 3.3 :At about -30° C., d11-(1-Bromocyclopentyl)-(2-chlorophenyl)-methanone (450 mg, 1.52 mmol) was treated with liquid d3methylamine (about 2 mL). After about 1 hour, the excess methylamine was evaporated, and the resulting residue was dissolved in hexane and re-evaporated. The residue was dissolved in diethyl ether (10 mL), and hydrochloride, gas was pumped in. The resulting precipitate was collected by filtration to give the title product (150 mg, 35percent). 1H NMR (300 MHz, CD3OD) δ 7.76-7.54 (m, 4H); LC-MS: m/z=249 (MH)+. With hydrogenchloride in diethyl ether Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/268071; (2008); (A1) English View in Reaxys
Cl
N
HO
Rx-ID: 7030657 View in Reaxys 6/7 Yield
Conditions & References 1-Br-Cyclopentyl-o-Cl-Ph-keton X, MeNH2
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Patent; Parke; Davis and Co.; US3254124; (1966); ; vol. 65; nb. 5414h; (1966) View in Reaxys o-Chlorphenylcyclopentylketon, 1. Br2, 2. CH3NH2 Patent; Parke; Davis and Co.; CH454128; (1963); Chem. Zentralbl. View in Reaxys
Cl
N
HO
Rx-ID: 7402980 View in Reaxys 7/7 Yield
Conditions & References Bromketon (VI), CH3-NH2 Patent; Stevens; BE634208; (1962); ; vol. 61; nb. 5569c; (1964) View in Reaxys
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