Putrescine → HCID 13772555, compound

HRID 986316Notes

Reaction equation

HRID 986316 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].[N+](C1C=CC([O:16][C:17](=O)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:33])=CC=1)([O-])=O>C(Cl)Cl.CO>[ClH:32].[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:17](=[O:16])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33]

Participants

4

Reactant 2

HCID 1045PutrescineHCID 203870824-Nitrophenyl 2-(2,6-dichlorophenyl-amino)-phenyl-acetate

Product 1

HCID 13772555HCID 13772555, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

1,4-diaminobutane and 2-{2-[(2,6-dichlorophenyl)-amino]-phenyl}-acetic acid p-nitrophenyl ester are allowed to react for 8 hours at room temperature in methylene chloride/methanol (1:1). The reaction solution is then concentrated by evaporation in vacuo, the residue is taken up in tetrahydrofuran and the whole is extracted by shaking with 2N hydrochloric acid. The aqueous phase is extracted three times with diethyl ether to remove nitrophenol and is then saturated with NaCl and extracted with tetrahydrofuran. The organic phase is dried with Na2SO4 and concentrated by evaporation. The residue is triturated with diethyl ether and yields a crystalline powder which is recrystallised from ethyl acetate. 2-{2-[(2,6-dichlorophenyl)-amino]-phenyl}-acetic acid 4aminobutylamide hydrochloride is obtained in the form of its ethyl acetate solvate; m.p. 137°-140°; Rf =0.177 (CHCl3 :methanol:concentrated aqueous ammonia solution=10:10:0.1).

Workup

  1. concentrationThe reaction solution is then concentrated by evaporation in vacuo
  2. extractionthe whole is extracted
  3. extractionThe aqueous phase is extracted three times with diethyl ether
  4. customto remove nitrophenol
  5. extractionsaturated with NaCl and extracted with tetrahydrofuran
  6. dry with materialThe organic phase is dried with Na2SO4
  7. concentrationconcentrated by evaporation
  8. customThe residue is triturated with diethyl ether
  9. customyields a crystalline powder which
  10. customis recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-0688969f34bc4c6db315078a528e9b03
Source dataset
uspto-grants-1987_12
Patent number
US04711879

Reaction notes

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