Acetone → N-(1-cyclopentyl-2-pyrrolidinyl methyl)-2,4-dimethoxy-5-methylsulphonyl benzamide

HRID 652785Notes

Reaction equation

HRID 652785 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:8][C:4]=1[C:5]([OH:7])=O.CC(C)=O.ClC(OCC(C)C)=O.[CH:30]1([N:35]2[CH2:39][CH2:38][CH2:37][CH:36]2[CH2:40][NH2:41])[CH2:34][CH2:33][CH2:32][CH2:31]1>C(N(CC)CC)C.O>[CH:30]1([N:35]2[CH2:39][CH2:38][CH2:37][CH:36]2[CH2:40][NH:41][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([S:14]([CH3:17])(=[O:16])=[O:15])[C:10]([O:12][CH3:13])=[CH:11][C:3]=2[O:2][CH3:1])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 62365Isobutyl chloroformateHCID 198601501-Cyclopentyl-2-aminomethylpyrrolidineHCID 214770622,4-Dimethoxy-5-methylsulfonylbenzoic acid

Product 1

HCID 20196883N-(1-cyclopentyl-2-pyrrolidinyl methyl)-2,4-dimethoxy-5-methylsulphonyl benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

91 g of 2,4-dimethoxy-5-methylsulphonyl benzoic acid, 400 ml of acetone, 130 ml of water and 48.6 ml of triethylamine are placed in a liter flask fitted with an agitator, a thermometer and a dropping funnel. 47.6 g of isobutyl chloroformate is dripped into the solution obtained, at about 10° C. It is agitated for 40 minutes, then 58.8 g of 1-cyclopentyl-2-aminomethyl-pyrrolidine is poured in drop by drop at about 0° C. A precipitate appears after 30 minutes of agitation at room temperature. It is allowed to react then the precipitate is filtered off, washed with water and dried. 74 g of a crude version of the product is obtained, melting at 198° C.

Workup

  1. customfitted with an agitator
  2. customobtained, at about 10° C
  3. waitA precipitate appears after 30 minutes of agitation at room temperature
  4. customto react
  5. filtrationthe precipitate is filtered off
  6. washwashed with water
  7. customdried
  8. custom74 g of a crude version of the product is obtained

Sources & evidence

ORD record
ord-3e00f87a5400402db2583947d444b4dc
Source dataset
uspto-grants-1987_06
Patent number
US04673686

Reaction notes

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