Triethylamine → 3-fluoro-N-(1-methyl-1-phenylethyl)benzamide

HRID 21070

Reaction equation

HRID 21070 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C:11]([NH2:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:20][C:11]([CH3:13])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:12])=[O:6]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68509CumylamineHCID 743763-Fluorobenzoyl chloride

Product 1

HCID 474447463-fluoro-N-(1-methyl-1-phenylethyl)benzamideYield 95.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 16, 3-fluorobenzoyl chloride (2.00 g, 12.6 mmol) was dissolved in dichloromethane (40 mL), and the solution was treated with cumylamine (1.99 mL, 13.9 mmol), triethylamine (2.63 mL, 18.9 mmol) and DMAP (154 mg, 1.26 mmol). The mixture was purified by slurry using diisopropylether to obtain 3-fluoro-N-(1-methyl-1-phenylethyl)benzamide (3.09 g, yield 95%).

Workup

  1. customThe mixture was purified by slurry

Sources & evidence

ORD record
ord-604da105a25148b5894cebf65055674a
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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