Methylamine → N,3-Dimethylbut-3-en-1-amine

HRID 1871174Notes

Reaction equation

HRID 1871174 reaction equation
[CH3:1][CH2:2]/[C:3](/[CH3:12])=[CH:4]/[CH2:5][CH2:6]/[C:7](/[CH3:11])=[CH:8]/[CH2:9][NH2:10].[CH2:13](Br)/[CH:14]=[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])\[CH3:16].[CH3:24][NH2:25].[K].[CH2:27]([NH:45][C:46](=O)C)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]/[CH:35]=[CH:36]\[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>C(O)C.C(OCC)C>[CH3:13][CH2:14][C:15]([CH3:17])=[CH:16][CH2:1][CH2:2][C:3]([CH3:12])=[CH:4][CH2:5][CH2:6][C:7]([CH3:11])=[CH:8][CH2:9][NH2:10].[CH3:27][NH:45][CH2:13][CH2:14][CH:15]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH3:16].[CH3:46][NH:45][CH2:27][CH2:28][C:29]([CH3:1])=[CH2:30].[CH3:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]/[CH:35]=[CH:34]\[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:24][NH2:25]

Participants

10

Reactant 4

HCID 6329MethylamineHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-HCID 86755596HCID 86755596, compoundHCID 87871347HCID 87871347, compound

Product 4

HCID 13212923N,3-Dimethylbut-3-en-1-amineHCID 22251448280755-56-8HCID 86755593HCID 86755593, compoundHCID 86755594HCID 86755594, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

N-methylgeranylamine used in the examples was prepared by treatment of geranyl bromide with 12 fold excess of methylamine in ethanol. The product was isolated by extraction into ethyl ether and distillation. N-methylfarnesylamine, N-methylcitronellylamine and N-methyl-3-methyl-3-butenylamine are prepared in a similar manner. N-methyloleylamine was prepared by methylation of the N-oleylacetamide potassium salt followed by hydrolysis.

Workup

  1. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-7b902f8254c843fd84f680f8fcd79537
Source dataset
uspto-grants-2000_08
Patent number
US06103322

Reaction notes

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