Iodoethane → Rac-n-(1-ethyl-3-phenyl-piperidin-3-yl)-2-methoxy-4,6-bis-trifluoromethyl-benzamide

HRID 2177534Notes

Reaction equation

HRID 2177534 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[C:4]=1[C:5]([NH:7][C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]1)=[O:6].[CH2:32](N(C(C)C)C(C)C)[CH3:33].ICC>ClCCl>[CH2:32]([N:10]1[CH2:11][CH2:12][CH2:13][C:8]([NH:7][C:5](=[O:6])[C:4]2[C:20]([C:28]([F:31])([F:29])[F:30])=[CH:21][C:22]([C:24]([F:25])([F:26])[F:27])=[CH:23][C:3]=2[O:2][CH3:1])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:9]1)[CH3:33]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 59438392HCID 59438392, compound

Product 1

HCID 59438481Rac-n-(1-ethyl-3-phenyl-piperidin-3-yl)-2-methoxy-4,6-bis-trifluoromethyl-benzamideYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 25.mg (0.056 mmol) rac-2-methoxy-N-(3-phenyl-piperidin-3-yl)-4,6-bis-trifluoromethyl-benzamide in 0.25 ml dichloromethane were added 19.7 ul (0.112 mmol) N-ethyldiisopropylamine and finally 6.0 ul (0.0728 mmol) iodoethane. The solution was stirred at room temperature for 20 hours. The solvent was removed in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 15 mg (58%) of the title compound as a colorless oil. MS (m/e): 475.2 (M+H).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-763d746e564f4387b84ea70cba43d98c
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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