Cyclobutanecarbonyl chloride → HCID 12804761, compound

HRID 1648911Notes

Reaction equation

HRID 1648911 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:26]([Cl:28])=[O:27])[CH2:25][CH2:24][CH2:23]1>CCOCC>[ClH:28].[CH:22]1([C:26]([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:27])[CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 78705Cyclobutanecarbonyl chlorideHCID 12542600HCID 12542600, compound

Product 1

HCID 12804761HCID 12804761, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.0 g of 1-methyl-4-(α-phenyl-2-tolyl)-4-piperidinol, Example 1, is treated with 10 g of cyclobutanecarbonyl chloride with stirring and cooling. The reaction mixture is stirred for 48 hours at ambient temperature, diluted with 15 ml of ether and then stirred for 2 hours. The resulting precipitate is collected by suction filtration, the filter cake washed well with ether and dried in vacuo over sodium hydroxide pellets. The filter cake is recrystallized twice from an acetone-ether mixture to give colorless crystals, mp 194.5°-195° C. of 4-cyclobutylcarbonyloxy-1-methyl-4-(α-phenyl-2-tolyl)piperidine hydrochloride.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture is stirred for 48 hours at ambient temperature
  3. stirringstirred for 2 hours
  4. filtrationThe resulting precipitate is collected by suction filtration
  5. washthe filter cake washed well with ether
  6. dry with materialdried in vacuo over sodium hydroxide pellets
  7. customThe filter cake is recrystallized twice from an acetone-ether mixture

Sources & evidence

ORD record
ord-64f065441ecf4b549b3432a0f01fa6a1
Source dataset
uspto-grants-1983_11
Patent number
US04414219

Reaction notes

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