Acetyl chloride → HCID 21482397, compound

HRID 1415429Notes

Reaction equation

HRID 1415429 reaction equation
[CH:1]1([CH:4]2[CH2:8][CH:7]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[CH:6]([CH3:19])[NH:5]2)[CH2:3][CH2:2]1.[C:20](Cl)(=[O:22])[CH3:21].C(N(CC)CC)C>C1C=CC=CC=1>[C:20]([N:5]1[CH:6]([CH3:19])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=2)[CH2:8][CH:4]1[CH:1]1[CH2:2][CH2:3]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21482387HCID 21482387, compound

Product 1

HCID 21482397HCID 21482397, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

13 G of 2-cyclopropyl-4-(m-trifluoromethylphenyl)-5-methylpyrrolidine, 6 ml of acetyl chloride and 8 ml of triethylamine in 50 ml of anhydrous benzene is stirred at ambient temperature for 18 hours. Ice is added to the reaction mixture and the organic products are extracted with ether; the ethereal extract is washed with water, with 5% sodium hydroxide and then again with water, and dried over sodium carbonate to give 14.4 g of N-acetyl-2-cyclopropyl-4-(m-trifluoromethylphenyl)-5-methylpyrrolidine, which is dissolved in 50 ml of anhydrous tetrahydrofuran and added dropwise to a suspension of 2.9 g of lithium aluminium hydride in 75 ml of anhydrous tetrahydrofuran at reflux temperature. Refluxing is then continued for 4 hours. The excess double hydride is destroyed with cold ethyl acetate. After adding water and ice, the mixture is extracted with ether; the ethereal extract is washed with water and dried over sodium carbonate. After evaporation of the ether, vacuum distillation of the residue gives 9.7 g of N-ethyl-2-cyclopropyl-4-(m-trifluoromethylphenyl)-5-methylpyrrolidine as a liquid. Boiling point 0.3 = 115° C.

Workup

  1. additionIce is added to the reaction mixture
  2. extractionthe organic products are extracted with ether
  3. extractionthe ethereal extract
  4. washis washed with water, with 5% sodium hydroxide
  5. dry with materialagain with water, and dried over sodium carbonate

Sources & evidence

ORD record
ord-1d5c6b7e3e824090a847d603e8b88522
Source dataset
uspto-grants-1977_01
Patent number
US04005103

Reaction notes

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