Isoamylamine → HCID 20534887, compound
Reaction equation
[CH2:1]([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20])=[CH:12][CH:11]=1)([O-:9])=[O:8]>>[CH2:1]([NH:6][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1)[CH2:2][CH:3]([CH3:5])[CH3:4]Participants
Procedure
Isopentylamine was reacted with 4-(4-nitrophenyl)butanoyl chloride to provide N-isopentyl-4-(4-nitrophenyl)butyramide, which when reduced by reaction with diborane afforded N-isopentyl-4-(4-nitrophenyl)butylamine. Reaction of the latter compound with acetyl chloride under the conditions of Example 22 gave N-acetyl-N-isopentyl-4-(4-nitrophenyl)butylamine. Reaction of 21.8 g. of N-acetyl-N-isopentyl-4-(4-nitrophenyl)butylamine with 220 ml. of 1 M diborane in tetrahydrofuran provided, after workup according to the method of Example 22, 19.8 g. of N-ethyl-N-isopentyl-4-(4-nitrophenyl)butylamine. Reaction of the amine with para-toluenesulfonic acid in ethyl acetate afforded N-ethyl-N-isopentyl-4-(4-nitrophenyl)butylaminium tosylate. M.P. 78°-80° C.
Sources & evidence
- ORD record
- ord-422f9d04639d483686aaf9e71bef6aa3
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04336269
Reaction notes
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