Triethylamine → 1-Benzhydryl-N-methylazetidine-3-carboxamide

HRID 980719Notes

Reaction equation

HRID 980719 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:11][CH:10]([C:12](O)=[O:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21](N1C=CN=C1)([N:23]1C=CN=C1)=O.C(N(CC)CC)C.Cl.CN>C(#N)C>[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH2:11][CH:10]([C:12]([NH:23][CH3:21])=[O:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 27354401-(Diphenylmethyl)azetidine-3-carboxylic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 137728491-Benzhydryl-N-methylazetidine-3-carboxamideYield 114.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7.5 g (28 mmole) of 1-(diphenylmethyl)azetidine-3-carboxylic acid in 75 ml of acetonitrile was added 6.0 g (37 mmole) of 1,1'-carbonyldiimidazole. The reaction was heated at 60° C. for two hours and successively treated with 3.11 g (30.8 mmole) of triethylamine and 2.08 g (30.8 mmole) of methylamine hydrochloride. The reaction was stirred at 60° C. for an additional hour, the solvent evaporated in vacuo, and the residue dissolved in chloroform. After washing with water and drying over magnesium sulfate, the chloroform layer was evaporated in vacuo to give 9.0 g of 1-(diphenylmethyl)-N-methyl-3-azetidinecarboxamide, mp 103-107° C.

Workup

  1. customthe solvent evaporated in vacuo
  2. dissolutionthe residue dissolved in chloroform
  3. washAfter washing with water
  4. dry with materialdrying over magnesium sulfate
  5. customthe chloroform layer was evaporated in vacuo

Sources & evidence

ORD record
ord-0d33869746da422ba7df0a91acd1fcfd
Source dataset
uspto-grants-1987_01
Patent number
US04638067

Reaction notes

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