Water → [3-Chloro-4-(4-methyl-piperazin-1-yl)-phenyl]carbamic acid tert-butyl ester

HRID 1971229Notes

Reaction equation

HRID 1971229 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:22]N1C(=O)CCC1=O.O>C(O)(C)C>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]2)=[C:12]([Cl:22])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 66870210[4-(4-Methyl-piperazin-1-yl)-phenyl]carbamic acid tert-butyl ester

Product 1

HCID 66870439[3-Chloro-4-(4-methyl-piperazin-1-yl)-phenyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

583 mg (2 mmol) of [4-(4-methyl-piperazin-1-yl)-phenyl]-carbamic acid tert-butyl ester (Example 65c) are dissolved in 10 ml of isopropanol and 286 mg (2.1 mmol) of N-chlorosuccinimide are added. The solution is stirred for 1 h at r.t. and 100 ml of water are added. The suspension is extracted with EtOAc and the organic phase is washed with water, dried over MgSO4 and evaporated to dryness. The residue is purified by MPLC to provide the title compound. Title compound: ES-MS: 326.3 (M+H)+; analytical HPLC: tret=4.43 minutes (Grad 2).

Workup

  1. extractionThe suspension is extracted with EtOAc
  2. washthe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe residue is purified by MPLC

Sources & evidence

ORD record
ord-3d34a61082e748cc98b016bb6a9d84d2
Source dataset
uspto-grants-2013_04
Patent number
US08431592B2

Reaction notes

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