Chloride → HCID 86739636, compound

HRID 2418263Notes

Reaction equation

HRID 2418263 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.C(N([CH2:22][CH3:23])CC)C.[Cl-].C1([C:28](O)=[O:29])CC1.[CH2:31](Cl)Cl>C(OCC)C>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][C:13](=[C:28]=[O:29])[N:12]([CH:23]3[CH2:22][CH2:31]3)[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 312ChlorideHCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 15655Cyclopropanecarboxylic acidHCID 111280344-[3-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

Product 1

HCID 86739636HCID 86739636, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 9.1 g of 4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine and of 4.04 g of triethylamine in 40 ml of methylene chloride cooled to 0° C., a solution of 4.2 g of chloride of cyclopropanecarboxylic acid in 20 ml of methylene chloride is added dropwise, whilst ensuring that the temperature does not exceed 5° C. The reaction mixture is left for 30 minutes at 0°-5° C., then for one hour at room temperature. 200 ml of diethyl ether are added, the mixture is filtered, the organic phase is washed three times with water, dried and evaporated to dryness under reduced pressure. Thus, 11.5 g of 4-(3-trifluoromethylphenyl)-1-cyclopropyl-carbonyl-1,2,3,6-tetrahydropyridine are obtained: yellow/brown oil containing traces of impurities.

Workup

  1. customdoes not exceed 5° C
  2. waitfor one hour at room temperature
  3. filtrationthe mixture is filtered
  4. washthe organic phase is washed three times with water
  5. customdried
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6a3e135ba6d8416fbb753c4f162cbf9a
Source dataset
uspto-grants-1984_09
Patent number
US04472408

Reaction notes

Loading…