1-Decylpiperazine → HCID 54231837, compound

HRID 1646917Notes

Reaction equation

HRID 1646917 reaction equation
[CH2:1]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:17]([O:21][C:22]([N:24]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:25][C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:17]([O:21][C:22]([N:24]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:25][C:26]([N:14]1[CH2:13][CH2:12][N:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:16][CH2:15]1)=[O:27])=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 2305441-DecylpiperazineHCID 516892Sodium BicarbonateHCID 21905636N-(tert-Butoxycarbonyl)-N-phenylglycine

Product 1

HCID 54231837HCID 54231837, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A 2.3 g (8.64 mmoles) quantity of N,N,-dicyclohexylcarbodiimide was added to 20 ml of a solution of 2.0 g (7.35 mmoles) of N-decylpiperazine, 1.9 g (7.56 mmoles) of N-t-butoxycarbonylphenylglycine, 1.3 g (15.5 mmoles) of sodium hydrogen carbonate and 122 mg (1.0 mmole) of 4-dimethylaminopyridine in anhydrous methylene chloride. The mixture was stirred at room temperature for 12 hours. The precipitated crystals were collected by filtration and washed with methylene chloride. Mother liquor and the washings were concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=15:1), giving 2.8 g (yield: 83%) of 1-(N-t-butoxycarbonylphenylglycyl)-4-decylpiperazine.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with methylene chloride
  3. concentrationMother liquor and the washings were concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-4917d928fae1439b9264199cda846c3b
Source dataset
uspto-grants-1993_01
Patent number
US05182284

Reaction notes

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