p-Toluenesulfonic acid → HCID 20534900, compound

HRID 1156561Notes

Reaction equation

HRID 1156561 reaction equation
[CH2:1]([N:3]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])[CH3:2].C(NCCCCC1C=CC([N+]([O-])=O)=CC=1)CC(C)C.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47]([OH:50])(=[O:49])=[O:48])=[CH:43][CH:42]=1>C(OCC)(=O)C>[S:47]([C:44]1[CH:45]=[CH:46][C:41]([CH3:51])=[CH:42][CH:43]=1)([O-:50])(=[O:49])=[O:48].[CH2:1]([NH+:3]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)[CH2:4][CH2:5][CH:6]([CH3:7])[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12923073HCID 12923073, compoundHCID 20494492HCID 20494492, compound

Product 1

HCID 20534900HCID 20534900, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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-0ae813053bdc40289c10bf79e918844b
Source dataset
uspto-grants-1982_06
Patent number
US04336269

Reaction notes

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