Cyclopropanecarbonyl chloride → HCID 12804757, compound

HRID 1733320Notes

Reaction equation

HRID 1733320 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([OH:8])[CH2:4][CH2:3]1.[CH:22]1([C:25]([Cl:27])=[O:26])[CH2:24][CH2:23]1>CCOCC>[ClH:27].[CH:22]1([C:25]([O:8][C:5]2([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[O:26])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 12542600HCID 12542600, compound

Product 1

HCID 12804757HCID 12804757, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.0 g of 1-methyl-4-(α-phenyl-2-tolyl)-4-piperidinol, free base of Example 1, is treated with 8.15 ml of cyclopropane carboxylic acid chloride with stirring and cooling. The resulting suspension is stirred for 16 hours at ambient temperature and then diluted with 25 ml of ether and permitted to stand for 144 hours. The precipitate is collected by suction filtration and the filter cake washed with ether, dried in vacuo at 40° C. for 16 hours leaving colorless crystals which are recrystallized twice from isopropyl alcohol to give colorless crystals, mp 198°-200° C. of 4-cyclopropylcarbonyloxy-1-methyl-4-(α-phenyl-2-tolyl)piperidine hydrochloride.

Workup

  1. temperaturecooling
  2. stirringThe resulting suspension is stirred for 16 hours at ambient temperature
  3. filtrationThe precipitate is collected by suction filtration
  4. washthe filter cake washed with ether
  5. customdried in vacuo at 40° C. for 16 hours
  6. customleaving colorless crystals which
  7. customare recrystallized twice from isopropyl alcohol

Sources & evidence

ORD record
ord-fe47bd19e9514bb2a75236eafbb1b21b
Source dataset
uspto-grants-1980_12
Patent number
US04241071

Reaction notes

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