Sodium Carbonate → 2-[1-(tert-Butoxycarbonyl)-4-piperidinyl]-N-[4-(6-chloronaphthalene-2-sulfonyl)-2-oxo-1-piperazinyl]acetamide

HRID 2086242Notes

Reaction equation

HRID 2086242 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([NH:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][C:19]2=[O:24])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[Cl:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[CH:38]=[C:37]([S:42](Cl)(=[O:44])=[O:43])[CH:36]=[CH:35]2>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][C:15]([NH:17][N:18]2[CH2:23][CH2:22][N:21]([S:42]([C:37]3[CH:36]=[CH:35][C:34]4[C:39](=[CH:40][CH:41]=[C:32]([Cl:31])[CH:33]=4)[CH:38]=3)(=[O:43])=[O:44])[CH2:20][C:19]2=[O:24])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 106351296-Chloronaphthalene-2-sulfonyl chlorideHCID 227271312-[1-(tert-butoxycarbonyl)-4-piperidinyl]-N-(2-oxo-1-piperazinyl)acetamide

Product 1

HCID 227272472-[1-(tert-Butoxycarbonyl)-4-piperidinyl]-N-[4-(6-chloronaphthalene-2-sulfonyl)-2-oxo-1-piperazinyl]acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(4-benzyloxycarbonyl-2-oxo-1-piperazinyl)-2-[1-(tert-butoxycarbonyl)-4-piperidinyl]acetamide (840 mg) and 10% Pd/C (500 mg) in methanol (35 ml) was stirred at room temperature for 15 hours under a hydrogen atmosphere. The catalyst was filtered off and the reaction mixture was concentrated to obtain N-(2-oxo-1-piperazinyl)-2-[1-(tert-butoxycarbonyl)-4-piperidinyl]acetamide as a colorless syrup. A solution of the resultant 2-[1-(tert-butoxycarbonyl)-4-piperidinyl]-N-(2-oxo-1-piperazinyl)acetamide in ethyl acetate (40 ml) and a 10% aqueous solution of sodium carbonate (40 ml) was combined at 0° C. with 6-chloronaphthalene-2-sulfonyl chloride (470 mg) and stirred at room temperature for 30 minutes. The organic phase was separated, washed with brine, dried and concentrated to obtain a residue, which was purified by a column chromatography on a silica gel (ethyl acetate) and crystallized from ethyl acetate to obtain the title compound (420 mg) as colorless crystals.

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customto obtain a residue, which
  6. customwas purified by a column chromatography on a silica gel (ethyl acetate)
  7. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a161a752b73849f6ba59676a92a3fd75
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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