2-(4-Phenylpiperazin-1-yl)ethan-1-amine → HCID 12941059, compound

HRID 1659467Notes

Reaction equation

HRID 1659467 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[O:16]1[CH2:33][C@@H:17]1[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](OCC#N)=[O:28])=[CH:22][CH:21]=1>C1COCC1>[O:16]1[CH2:33][C@@H:17]1[CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][C:27]([NH:1][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)=[O:28])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 47425032-(4-Phenylpiperazin-1-yl)ethan-1-amineHCID 12941053HCID 12941053, compound

Product 1

HCID 12941059HCID 12941059, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.7 g (52.1 mmol) 1-(2-aminoethyl)-4-phenylpiperazine and 13.5 g (54.6 mmol) (R)-4-(2,3-epoxypropoxy)phenylacetic acid, cyanomethyl ester in 125 dry THF was stirred at room temperature for 40 hours. The solvent was removed in vacuo and the residue was triturated with ether to give the crude amide as a white solid. The solid was dissolved in 35 ml. CH2Cl2 and placed on a column of 170 g Woelm basic alumina (grade 3) made up in CHCl2. Elution with 1 liter CH2Cl2 furnished essentially pure material. Crystallization from acetone afforded the end product, m.p. 124°-125°. A second crop, m.p. 121°-123° was obtained from the mother liquors.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-a4d46d18cd78426aab0b9d2cb3237b2c
Source dataset
uspto-grants-1981_12
Patent number
US04304721

Reaction notes

Loading…