Triethylamine → HCID 13772850, compound

HRID 868118Notes

Reaction equation

HRID 868118 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]([OH:14])=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)([N:23]1[CH:27]=[CH:26]N=C1)=O.C(N(CC)CC)C.Cl.C(N)C>C(#N)C>[C:1]1([CH:7]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:8]2[CH2:9][CH:10]([C:12]([NH:23][CH2:27][CH3:26])=[O:14])[CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 27354401-(Diphenylmethyl)azetidine-3-carboxylic acid

Product 1

HCID 13772850HCID 13772850, compoundYield 114%

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 3.1 g (30.8 mmole) of triethylamine and 2.52 g (30.8 mmole) of ethylamine 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 9.4 g of 1-(diphenylmethyl)-N-ethyl-3-azetidinecarboxamide, mp 91°-93° 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-5cd222c478554faab65a75aa4be7cbfe
Source dataset
uspto-grants-1988_10
Patent number
US04777175

Reaction notes

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