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

HRID 1670482Notes

Reaction equation

HRID 1670482 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-3517995b6d824946853c26bbf1fb2d67
Source dataset
uspto-grants-2011_08
Patent number
US07994170B2

Reaction notes

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