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

HRID 21074

Reaction equation

HRID 21074 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[C:12]([NH2:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])[CH3:13].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:21][C:12]([CH3:14])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13])=[O:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 68509CumylamineHCID 74374m-Anisoyl chloride

Product 1

HCID 474447523-methoxy-N-(1-methyl-1-phenylethyl)benzamideYield 98.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Step 1 of Example 16, 3-methoxybenzoylchloride (8.00 g, 46.9 mmol) was dissolved in dichloromethane (160 mL), and the solution was treated with cumylamine (7.40 mL, 51.6 mmol), triethylamine (9.80 mL, 70.4 mmol) and DMAP (573 mg, 4.69 mmol), followed by purification by slurry using diisopropylether to obtain 3-methoxy-N-(1-methyl-1-phenylethyl)benzamide (12.4 g, yield 98%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-3ae2376e5a64468fa46f09c86691de66
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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