4-[3-(Benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester → Tert-butyl 4-(3-sulfamoylpropyl)piperazine-1-carboxylate

HRID 1894368Notes

Reaction equation

HRID 1894368 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][S:17](=[O:33])(=[O:32])[NH:18]C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][S:17](=[O:32])(=[O:33])[NH2:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 672053494-[3-(Benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67205279Tert-butyl 4-(3-sulfamoylpropyl)piperazine-1-carboxylateYield 79.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-[3-(benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester (650 mg, 1.37 mmol) and palladium hydroxide (1.154 g, 1.64 mmol, 20% w from Aldrich) in methanol (10 mL) was hydrogenated at room temperature overnight using a Parr apparatus (50 psi). The reaction mixture was filtered through a Celite cake, and the filtrate was concentrated. Purification of the crude residue by flash column chromatography (40 g of silica gel, eluting with methanol and ethyl acetate) gave 4-(3-sulfamoyl-propyl)-piperazine-1-carboxylic acid tert-butyl ester as an off-white solid (334 mg).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite cake
  2. concentrationthe filtrate was concentrated
  3. customPurification of the crude residue
  4. washby flash column chromatography (40 g of silica gel, eluting with methanol and ethyl acetate)

Sources & evidence

ORD record
ord-4a75503c7a394b4191d51d95743348e6
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

Loading…