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

HRID 894975Notes

Reaction equation

HRID 894975 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-c7ded445533f4d96b2b7fc16b7464876
Source dataset
uspto-grants-1981_08
Patent number
US04285873

Reaction notes

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