Water → N-[4-[3-(1-adamantyl)-4-methoxy benzamido]-benzoyl]pyrrolidine

HRID 249030

Reaction equation

HRID 249030 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22]12([C:32]3[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=3[O:41][CH3:42])[C:35](Cl)=[O:36])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2.O>ClCCl>[C:22]12([C:32]3[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=3[O:41][CH3:42])[C:35]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([N:8]4[CH2:9][CH2:10][CH2:11][CH2:12]4)=[O:7])=[CH:13][CH:14]=3)=[O:36])[CH2:23][CH:24]3[CH2:30][CH:28]([CH2:27][CH:26]([CH2:25]3)[CH2:31]1)[CH2:29]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5778004-(Pyrrolidin-1-ylcarbonyl)anilineHCID 108044973-(1-Adamantyl)-4-methoxybenzoyl chloride

Product 1

HCID 19762696N-[4-[3-(1-adamantyl)-4-methoxy benzamido]-benzoyl]pyrrolidineYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.7 g (9 mmoles) of N-p-aminobenzoyl pyrrolidine and 1 g (10 mmoles) of triethylamine are dissolved in 30 ml of dichloromethane. With stirring, 2.8 g (9 mmoles) of 3-(1-adamantyl)-4-methoxybenzoyl chloride dissolved in 60 ml of dichloromethane are added. The reaction mixture is stirred for 16 hours, at which point water is added and the reaction mixture is extracted with dichloromethane. The extract is washed with water, extracted with methylene chloride and dried on MgSO4. The solvents are evaporated and the residue (yellow foam) is crystallized in ethyl acetate to give 3.0 g (73% yield) of N-[4-[3-(1-adamantyl)-4-methoxy benzamido]-benzoyl] pyrrolidine which melts at 239°-242° C.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred for 16 hours, at which
  3. additionis added
  4. extractionthe reaction mixture is extracted with dichloromethane
  5. washThe extract is washed with water
  6. extractionextracted with methylene chloride
  7. customdried on MgSO4
  8. customThe solvents are evaporated
  9. customthe residue (yellow foam) is crystallized in ethyl acetate

Sources & evidence

ORD record
ord-c48105e083704c33a04f4f9408d6ac74
Source dataset
uspto-grants-1993_05
Patent number
US05212203

Linked notes

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