[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amine → N-[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]-2-(methylthio)-4,6-bis(trifluoromethyl)benzamide

HRID 20851Notes

Reaction equation

HRID 20851 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[C:4]=1[C:5](Cl)=[O:6].[CH3:20][C:21]([N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)([CH3:30])[CH:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:30][C:21]([N:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1)([CH3:20])[CH:22]([NH:29][C:5](=[O:6])[C:4]1[C:8]([C:16]([F:19])([F:18])[F:17])=[CH:9][C:10]([C:12]([F:15])([F:14])[F:13])=[CH:11][C:3]=1[S:2][CH3:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 25158607[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amineHCID 59347928HCID 59347928, compound

Product 1

HCID 59347805N-[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]-2-(methylthio)-4,6-bis(trifluoromethyl)benzamideYield 85%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(methylthio)-4,6-bis(trifluoromethyl)benzoyl chloride D55 (60 mg; 0.19 mmol) in dry DCM (1 ml) was treated with (+)-[2-methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amine D6 (60 mg, 0.27 mmol) followed by triethylamine (5drops) and left overnight at room temperature. The volatile components were removed under reduced pressure and the residue chromatographed on silica gel. Elution with 0-80% ethyl acetate in pentane gave the title product as an oil (80 mg, 85%). 1H NMR (CDCl3) δ: 0.94 (3H, s), 1.00 (3H, s), 1.69 (4H, overlapping m), 2.54 (3H, s), 2.62 (2H, m), 2.72 (2H, m), 4.78 (1H, s), 7.25-7.45 (6H, overlapping m), 7.68 (1H, s), 7.72 (1H, s). Mass Spectrum (Electrospray LC/MS): Found 505 (MH+) C24H26F6N2OS requires 504. Ret time 2.24 min.

Workup

  1. customThe volatile components were removed under reduced pressure
  2. customthe residue chromatographed on silica gel
  3. washElution with 0-80% ethyl acetate in pentane

Sources & evidence

ORD record
ord-88907c530e6d4ce8a7ff9609deb5ba75
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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