Putrescine → HCID 20532078, compound

HRID 1759455Notes

Reaction equation

HRID 1759455 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[NH2:7]CCN1CCNCC1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](=O)[CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:19][CH:18]=1.[C:36](#N)[CH:37]=[CH2:38]>>[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([NH2:7])([NH2:6])[CH2:36][CH2:37][CH2:38][CH:25]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[CH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 1045PutrescineHCID 7855AcrylonitrileHCID 8795AminoethylpiperazineHCID 13022432HCID 13022432, compound

Product 1

HCID 20532078HCID 20532078, compound

Procedure

An an alternative to obtaining a mixture of Schiff bases VI and VI(a) or VI(b), which upon reduction give a mixture of product I the reaction can be conducted stepwise. For example, 1,4-diaminobutane or 4-(2-aminoethyl)piperazine may be converted to a Schiff base with 1,5-di-(4-chloro-phenyl)-3-pentanone, catalytically reduced, then the resulting amine selectively cyanoethylated with acrylonitrile, followed by catalytic hydrogenation to furnish 1-(3-aminopropyl)-4-[1,5-di-(4-chloro-phenyl)-3-pentyl]diaminobutane, a spermidine derivative, or 1-(3-aminopropyl)-4-[2(1,5-di-(4-chloro-phenyl)-3-pentylamino ethyl]piperazine. A primary amine can be dicyanoethylated with excess acrylonitrile, catalytically reduced to the corresponding 3,3'-substituted iminobis(propylamine) and then converted by condensation with a ketone and reduction to the N-alkylated-3,3'-substituted iminobis(propylamine). For example, dicyanoethylation of monoethanolamine followed by catalytic reduction provides 3,3'-(2-hydroxyethylimino)bis(propylamine). Condensation with 1-(2,4-dimethylphenyl)-6-(3-chlorophenyl)-3-hexanone and subsequent catalytic hydrogenation of the --C=N bond affords 1-[1-(2,4-dimethylphenyl)-6-(3-chlorophenyl)-3-hexyl]-5-(2-hydroxyethyl)-1,5,9-triazanonane.

Workup

  1. customAn an alternative to obtaining
  2. customgive
  3. customthe reaction

Sources & evidence

ORD record
ord-1235c8eda24241bd83830cffd8e8d352
Source dataset
uspto-grants-1982_07
Patent number
US04340756

Reaction notes

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