Putrescine → HCID 23467831, compound

HRID 461099Notes

Reaction equation

HRID 461099 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[NH2:7]CCN1CCNCC1.[CH:16]([C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](=O)[CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)=[CH:21][CH:20]=1)([CH3:18])[CH3:17].[C:40](#N)[CH:41]=[CH2:42]>>[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([NH2:7])([NH2:6])[CH2:40][CH2:41][CH2:42][CH:27]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=1)[CH2:26][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([CH:16]([CH3:18])[CH3:17])=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 1045PutrescineHCID 7855AcrylonitrileHCID 8795AminoethylpiperazineHCID 12797296HCID 12797296, compound

Product 1

HCID 23467831HCID 23467831, compound

Procedure

As 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-isopropyl-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-isopropylphenyl)-3-pentyl]diaminobutane, a spermidine derivative, or 1-(3-aminopropyl)-4-[2{(1,5-di-(4-isopropylphenyl)-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-isopropylphenyl)-3-hexanone and subsequent catalytic hydrogenation of the --C=N bond affords 1-[1-(2,4-dimethylphenyl)-6-(3-isopropylphenyl)-3-hexyl]-5-(2-hydroxyethyl)-1,5,9-triazanonane.

Workup

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

Sources & evidence

ORD record
ord-9c1ca355c8cd46fd948ae27338962682
Source dataset
uspto-grants-1977_12
Patent number
US04061775

Reaction notes

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