Acrylonitrile → HCID 20363697, compound

HRID 1679106Notes

Reaction equation

HRID 1679106 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1.[CH:11]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22](=O)[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)=[CH:16][CH:15]=1)([CH3:13])[CH3:12].[C:35](#[N:38])[CH:36]=[CH2:37]>>[NH2:38][CH2:35][CH2:36][CH2:37][N:7]1[CH2:8][CH2:9][CH2:10][CH:5]([CH2:4][CH2:3][CH2:2][NH:1][CH:22]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[CH2:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([CH:11]([CH3:13])[CH3:12])=[CH:15][CH:16]=2)[CH2:6]1

Participants

4

Reactant 3

HCID 7855AcrylonitrileHCID 122475763-Piperidin-3-yl-propylamineHCID 12797296HCID 12797296, compound

Product 1

HCID 20363697HCID 20363697, compound

Procedure

For example, 3-(3-aminopropyl)piperidine may be converted to a Schiff base with 1,5-di-(4-isopropylphenyl)-3-pentanone, catalytically reduced, then the resulting amine selectively cyanoethylated on the ring nitrogen with acrylonitrile, followed by catalytic hydrogenation to furnish 1-(3-aminopropyl)-3-{3-[1,5-di-(4-isopropylphenyl)-3-pentylamino]propyl}piperidine.

Sources & evidence

ORD record
ord-d86e62b99f4948a1aa82f067e59b2f2d
Source dataset
uspto-grants-1978_03
Patent number
US04079059

Reaction notes

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