N,N-Diethyl-1-heptanamine → (Z)-4-(4-Chlorophenyl)-N,N-diethyl-N-heptyl-2-buten-1-aminium 4-methylbenzenesulfonate

HRID 464035Notes

Reaction equation

HRID 464035 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11]O)=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O-:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.[CH2:24]([N:26]([CH2:34][CH3:35])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH3:25]>C(#N)C>[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([O-:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]/[CH:9]=[CH:10]\[CH2:11][N+:26]([CH2:24][CH3:25])([CH2:34][CH3:35])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12496130N,N-Diethyl-1-heptanamineHCID 131714350(Z)-4-(4-Chlorophenyl)-2-buten-1-ol 4-methylbenzenesulfonate

Product 1

HCID 13660242(Z)-4-(4-Chlorophenyl)-N,N-diethyl-N-heptyl-2-buten-1-aminium 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Mix 5.40 g (0.016 mole) of (Z)-4-(4-chlorophenyl)but-2-en-1-ol 4-methylbenzenesulfonate and 10.96 g (0.064 mole) of N,N-diethylheptanamine in 200 ml of acetonitrile. Stir the mixture at room temperature for 2 hours. Evaporate and recrystallize from ethyl acetate to yield the title compound, m.p. 79°-80° C.

Workup

  1. customEvaporate
  2. customrecrystallize from ethyl acetate

Sources & evidence

ORD record
ord-2d2e8ee335394a5fb66d31299340c9f4
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Reaction notes

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