7-Bromooct-1-ene → n-Methyloct-5-en-1-amine tosylate salt

HRID 925918Notes

Reaction equation

HRID 925918 reaction equation
Br[CH:2]([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].[S:10]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)([OH:13])(=[O:12])=[O:11].[CH3:21][NH:22]CCCCC=C>>[S:10]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)([OH:13])(=[O:12])=[O:11].[CH3:21][NH:22][CH2:9][CH2:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 221384327-Bromooct-1-eneHCID 46737741N-methylhex-5-en-1-amine 4-methylbenzenesulfonate

Product 1

HCID 131729113n-Methyloct-5-en-1-amine tosylate salt

Procedure

N-Methyloct-5-en-1-amine tosylate salt 31c was synthesized from 7-bromo-octene, according to the procedure as described for compound 31a, as a white powder in quantitative yield. 1H NMR (CDCl3, 400 MHz) δ 1.38 (q, J=7.76 Hz, 2H), 1.71 (q, J=7.76 Hz, 2H), 1.80 (q, J=6.98 Hz, 2H), 1.90 (q, J=6.9 Hz, 2H), 1.99 (q, J=6.98 Hz, 2H), 2.38 (s, 3H), 2.70 (t, J=5.17 Hz, 3H), 2.87-2.93 (m, 2H), 4.92-4.99 (m, 2H), 5.67-5.73 (m, 1H), 7.20 (d, J=7.76 Hz, 2H), 7.75 (d, J=7.76 Hz, 2H), 8.62 (brs, 2H).

Sources & evidence

ORD record
ord-2a976d3e45c3493a930969cc6c4ebba7
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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