Benzoyl chloride → N-(2-methyl-2-phenylpropyl)benzamide

HRID 383991Notes

Reaction equation

HRID 383991 reaction equation
CCN(CC)CC.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[CH3:18][C:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH2:20][NH2:21]>C(Cl)Cl>[CH3:22][C:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:18])[CH2:20][NH:21][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 210601Phenethylamine, beta,beta-dimethyl-, hydrochloride

Product 1

HCID 13728589N-(2-methyl-2-phenylpropyl)benzamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.0 ml (30 mmol) of NEt3 and 4.22 g (30 mmol) of benzoylchloride were added in succession at 0° C. to a solution of 1.86 g (10.0 mmol) of 2-methyl-2-phenylpropylamine hydrochloride in DCM (30 ml) and the mixture was stirred for 1 h at RT. It was then diluted with DCM and washed with a 10% aqueous hydrochloric acid, a saturated aqueous Na2CO3 solution and brine. The organic phase was dried over Na2SO4, filtered and concentrated to small volume under vacuum. 2.48 g (9.8 mmol, 98%) of N-(2-methyl-2-phenylpropyl)benzamide were obtained as the residue, which was reacted further with no additional purification.

Workup

  1. washwashed with a 10% aqueous hydrochloric acid
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-9a588c00e16c4c149385269ef7f155a7
Source dataset
uspto-grants-2013_02
Patent number
US08367700B2

Reaction notes

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