9-Fluorenylmethyl chloroformate → HCID 131724191, compound

HRID 478442Notes

Reaction equation

HRID 478442 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C@H:10]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:27]1[C:39]2[CH:38]([CH2:40][O:41][C:42](Cl)=[O:43])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]=2[CH:30]=[CH:29][CH:28]=1>ClCCl.C(=O)(O)[O-].[Na+]>[CH:27]1[C:39]2[CH:38]([CH2:40][O:41][C:42]([N:17]3[CH2:18][CH2:19][N:14]([C@H:11]4[CH2:12][CH2:13][N:8]([CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH2:9][C@H:10]4[C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=4)[CH2:15][CH2:16]3)=[O:43])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]=2[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 131724190HCID 131724190, compound

Product 1

HCID 131724191HCID 131724191, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Rac-cis-1-[1-Benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-piperazine (2.00 g, 5.41 mmol) was dissolved in dichloromethane (130 mL) and 9-fluorenylmethyl-chloroformate (1.71 g, 6.49 mmol) in dichloromethane (50 mL) was added at 0° C. The reaction mixture was stirred at room temperature overnight and diluted with sat sodium bicarbonate solution (100 mL). The organic phase was separated and the aqueous layer was extracted twice with 150 mL dichloromethane. Organic phases were pooled, dried with magnesium sulfate and evaporated. Flash chromatography on silica gel with cyclohexane/ethyl acetate 6:1 gave rac-cis-4-[1-benzyl-3-(4-chloro-phenyl)-piperidin-4-yl]-piperazine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (1.75 g, 55%) as a light yellow solid, MS: m/e=592.3 (M+).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted twice with 150 mL dichloromethane
  3. dry with materialdried with magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-64c2981a6f9644b68a884f861fd8f922
Source dataset
uspto-grants-2003_11
Patent number
US06642226B2

Reaction notes

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