1-Phenylpiperazine → HCID 21563356, compound

HRID 1580624Notes

Reaction equation

HRID 1580624 reaction equation
CC([CH2:6][C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([F:16])=[CH:11][CH:10]=2)C(O)=O.[CH2:17](N(CC)CC)C.ClC([O:27][CH2:28][CH3:29])=O.[C:30]1([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[CH3:6][C:7]1[NH:8][C:9]2[C:14]([C:15]=1[CH2:17][CH2:29][C:28]([N:39]1[CH2:40][CH2:41][N:36]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:37][CH2:38]1)=[O:27])=[CH:13][C:12]([F:16])=[CH:11][CH:10]=2

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 68138085HCID 68138085, compound

Product 1

HCID 21563356HCID 21563356, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 66.2 g of 2-methyl-5-fluoro-3-indolylpropionic acid and 30.3 g of triethylamine in 400 ml of tetrahydrofuran was added dropwise 32.6 g of ethyl chloroformate at a temperature below 0°C. The stirring was continued for additional 30 minutes below 0°C and thereto was added dropwise a solution of 48.7 g of 4-phenylpiperazine in 100 ml of tetrahydrofuran. After addition was completed, the reaction mixture was stirred for 4 hours at room temperature and then filtered. The filtrate was concentrated under reduced pressure to a residual solid, which was recrystallized from ethanol to give 1-[β-(2-methyl-5-fluoro-3-indolyl)propionyl]-4-phenylpiperazine, melting at 170.0°-171.5°C.

Workup

  1. additionAfter addition
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure to a residual solid, which
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-e5f60f9e36464a6e9fe18ce9bc45947d
Source dataset
uspto-grants-1976_01
Patent number
US03933824

Reaction notes

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