Cyclopropanecarbonyl chloride → N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylcyclopropanecarboxamide hydrochloride

HRID 1973828Notes

Reaction equation

HRID 1973828 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5]1.[CH:25]1([C:28]([Cl:30])=[O:29])[CH2:27][CH2:26]1>CC1C=CC=CC=1>[ClH:30].[CH3:1][O:2][CH2:3][C:4]1([N:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:28]([CH:25]2[CH2:27][CH2:26]2)=[O:29])[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 122982104-Piperidinamine, 4-(methoxymethyl)-N-phenyl-1-(2-phenylethyl)-

Product 1

HCID 12298133N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylcyclopropanecarboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred mixture of 3.25 parts of 4-(methoxymethyl)-N-phenyl-1-(2-phenylethyl)-4-piperidinamine and 36 parts of dry methylbenzene is added a mixture of 1.25 parts of cyclopropanecarbonyl chloride and 9 parts of dry methylbenzene at room temperature. The whole is stirred and refluxed for 3 hours. The reaction mixture is filtered hot and upon cooling, the product is allowed to crystallize from the filtrate. It is filtered off, washed with 2,2'-oxybispropane and dried, yielding N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylcyclopropanecarboxamide hydrochloride; mp. 178.6° C.

Workup

  1. additionis added
  2. temperaturerefluxed for 3 hours
  3. filtrationThe reaction mixture is filtered hot
  4. temperatureupon cooling
  5. customto crystallize from the filtrate
  6. filtrationIt is filtered off
  7. washwashed with 2,2'-oxybispropane
  8. customdried

Sources & evidence

ORD record
ord-74dcf0918c424e0084a0fd4efe4e78cf
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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