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Sodium hydride → [2-(3,4-Dichloro-phenoxy)-5-(4-isopropyl-2-oxo-piperazin-1-ylmethyl)-benzyl]-methyl-carbamic acid tert-butyl ester

HRID 1454237
Notes
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Reaction equation

HRID 1454237 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][C:6](=[O:10])[CH2:5]1)([CH3:3])[CH3:2].[H-].[Na+].[C:13]([O:17][C:18](=[O:39])[N:19]([CH2:21][C:22]1[CH:27]=[C:26]([CH2:28]Cl)[CH:25]=[CH:24][C:23]=1[O:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)[CH3:20])([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[C:13]([O:17][C:18](=[O:39])[N:19]([CH2:21][C:22]1[CH:27]=[C:26]([CH2:28][N:7]2[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][C:6]2=[O:10])[CH:25]=[CH:24][C:23]=1[O:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)[CH3:20])([CH3:16])([CH3:14])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 208238784-Isopropylpiperazin-2-oneHCID 68849807[5-Chloromethyl-2-(3,4-dichloro-phenoxy)-benzyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 68879733[2-(3,4-Dichloro-phenoxy)-5-(4-isopropyl-2-oxo-piperazin-1-ylmethyl)-benzyl]-methyl-carbamic acid tert-butyl esterYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

To a solution of 4-isopropyl-piperazin-2-one (32 mg, 0.22 mmol) in DMF (2.2 mL) at 0° C. was added NaH (90%, 11 mg). After 30 min, a solution of [5-chloromethyl-2-(3,4-dichloro-phenoxy)-benzyl]-methyl-carbamic acid tert-butyl ester (96 mg, 0.22 mmol) in DMF (2.2 mL) was added and the reaction was allowed to come to rt and stir overnight. The mixture was quenched with satd. aq. NaHCO3 and extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated. The crude product was purified by FCC to provide the desired product (94 mg, 79%). MS (ESI): mass calcd. for C27H35Cl2N3O4, 535.20; m/z found, 536.2 [M+H].

Workup

  1. customto come to rt
  2. customThe mixture was quenched with satd
  3. extractionaq. NaHCO3 and extracted with DCM
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-3c5efbbb638943b0a2dddaee555a3762
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07479493B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes