1-Naphthalenecarbonyl chloride → N-(1-Cyclohexyl-3-pyrrolidinyl)-N-methyl-1-naphthalenecarboxamide Hydrochloride

HRID 371618Notes

Reaction equation

HRID 371618 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([NH:12][CH3:13])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:14]1([C:24]([Cl:26])=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>C1C=CC=CC=1>[ClH:26].[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([N:12]([CH3:13])[C:24]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)=[O:25])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 701461-Naphthalenecarbonyl chlorideHCID 128957171-Cyclohexyl-N-methylpyrrolidin-3-amine

Product 1

HCID 20355406N-(1-Cyclohexyl-3-pyrrolidinyl)-N-methyl-1-naphthalenecarboxamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To 18.8 gm. (0.11 mole) of 1-cyclohexyl-3-methylaminopyrrolidine in dry benzene was added dropwise with stirring 19.0 gm. (0.10 mole) of 1-naphthalenecarbonyl chloride in dry benzene. The crystalline product which separated was collected and recrystallized from benzene to give 27.5 gm. (74%) of product which melted at 219°-221° C.

Workup

  1. customThe crystalline product which separated
  2. customwas collected
  3. customrecrystallized from benzene
  4. customto give 27.5 gm

Sources & evidence

ORD record
ord-87e0e23859024423a493a09d75a22431
Source dataset
uspto-grants-1978_05
Patent number
US04087428

Reaction notes

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