Ammonium Hydroxide → Morpholine, 4-(2-((2-(4-phenyl-1-piperazinyl)ethyl)amino)benzoyl)-, monohydrochloride

HRID 1439598Notes

Reaction equation

HRID 1439598 reaction equation
N[CH:2]1[O:7][CH2:6][CH2:5][N:4]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.Cl.[C:17]1([CH:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH2:24][Cl:25])[CH:22]=[CH:21][CH:20]=CC=1.[C:32]([O-])(=O)[CH3:33].[Na+].[NH4+:37].[OH-]>O>[ClH:25].[C:23]1([N:26]2[CH2:27][CH2:28][N:29]([CH2:33][CH2:32][NH:37][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8]([N:4]3[CH2:5][CH2:6][O:7][CH2:2][CH2:3]3)=[O:15])[CH2:30][CH2:31]2)[CH:24]=[CH:20][CH:21]=[CH:22][CH:17]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 517045Sodium AcetateHCID 53411132HCID 53411132, compoundHCID 70587860HCID 70587860, compound

Product 1

HCID 3050284Morpholine, 4-(2-((2-(4-phenyl-1-piperazinyl)ethyl)amino)benzoyl)-, monohydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

o-Aminobenzoylmorpholine (9 g), 14 g phenylpiperazinoethyl chloride hydrochloride, 12 g sodium acetate, and 50 ml water were refluxed 24 hours. The reaction was cooled to 30°, 100 ml water and 100 ml NH4OH added and the liquid decanted. The solid was stirred with 125 ml hot 60% propanol and filtered. The solid was dissolved in 1 liter of ether and 120 ml methanol and a solution of HCl gas in ether added to give 6.1 g, m.143-5°.

Workup

  1. temperatureThe reaction was cooled to 30°
  2. customthe liquid decanted
  3. filtrationfiltered
  4. dissolutionThe solid was dissolved in 1 liter of ether
  5. addition120 ml methanol and a solution of HCl gas in ether added
  6. customto give 6.1 g, m
  7. custom143-5°

Sources & evidence

ORD record
ord-a5a8003cc1cd4be7b98f6efe393e7c9d
Source dataset
uspto-grants-1977_11
Patent number
US04060526

Reaction notes

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