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Triethylamine → Benzyl 4-(2-(4-methoxyphenylthio)ethylcarbamoyl)piperazine-1-carboxylate

HRID 1917072
Notes
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Reaction equation

HRID 1917072 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.ClC(Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.[CH2:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])C.[C:32]([N:42]1CCCCC1)([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH:12][C:25]([N:27]2[CH2:30][CH2:31][N:42]([C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[CH2:29][CH2:28]2)=[O:16])=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 228749Benzyl piperidine-1-carboxylateHCID 12261932Ethanamine, 2-[(4-methoxyphenyl)thio]-

Product 1

HCID 68626717Benzyl 4-(2-(4-methoxyphenylthio)ethylcarbamoyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of compound 1 (183 mg) in CH2Cl2 (10 mL) was added triphosgene (0.7 eq.) and triethylamine (1.0 eq.) at 0° C. The reaction mixture was stirred for 1 h. at r.t., and N-Cbz-piperidine (1.5 eq.) and Et3N (0.5 mL) were added. The reaction mixture was stirred overnight and washed with 1N HCl and sat NaHCO3 (3×5 mL). The solvents were removed by evaporation under reduced pressure to give the title product 18, which was purified by chromatography (SiO2, CH2Cl2/EtOAc 10:1). Yield: 360 mg.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. washwashed with 1N HCl
  3. customThe solvents were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-44b55b8362cc4f0b951d1671d0c489a8
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618282B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes