Acrylonitrile → HCID 21425715, compound

HRID 258783Notes

Reaction equation

HRID 258783 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]([CH:14]1[CH:19]2[CH2:20][CH:16]([CH2:17][CH2:18]2)[CH:15]1[CH2:21][CH2:22][C:23](=O)[CH2:24][CH2:25][CH:26]1[CH:31]([CH:32]([CH3:34])[CH3:33])[CH:30]2[CH2:35][CH:27]1[CH2:28][CH2:29]2)([CH3:13])[CH3:12].[C:37](#[N:40])[CH:38]=[CH2:39]>>[NH2:40][CH2:37][CH2:38][CH2:39][N:7]1[CH2:8][CH2:9][CH2:10][CH:5]([CH2:4][CH2:3][CH2:2][NH:1][CH:23]([CH2:22][CH2:21][CH:15]2[CH:14]([CH:11]([CH3:13])[CH3:12])[CH:19]3[CH2:20][CH:16]2[CH2:17][CH2:18]3)[CH2:24][CH2:25][CH:26]2[CH:31]([CH:32]([CH3:34])[CH3:33])[CH:30]3[CH2:35][CH:27]2[CH2:28][CH2:29]3)[CH2:6]1

Participants

4

Reactant 3

HCID 7855AcrylonitrileHCID 122475763-Piperidin-3-yl-propylamineHCID 21425721HCID 21425721, compound

Product 1

HCID 21425715HCID 21425715, compound

Procedure

For example, 3-(3-aminopropyl)piperidine may be converted to a Schiff base with 1,5-di-(3-isopropylnorborn-2-yl)-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-(3-isopropylnorborn-2-yl)-3-pentylamino]propyl}piperidine.

Sources & evidence

ORD record
ord-8605dac52ee444388423bc96e9f1aabd
Source dataset
uspto-grants-1977_07
Patent number
US04033748

Reaction notes

Loading…