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Hydrochloric Acid → HCID 69265940, compound

HRID 2054454
Notes
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Reaction equation

HRID 2054454 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([CH3:11])=[CH:6][C:5]=1[NH:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>CN(C)C=O>[CH2:28]([N:12]([C:5]1[CH:6]=[C:7]([CH3:11])[C:8]([Cl:10])=[CH:9][C:4]=1[Br:3])[C:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 71127758HCID 71127758, compound

Product 1

HCID 69265940HCID 69265940, compound

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

Sodium hydride (193 mg, 8.06 mmol) was added to a stirred solution of tert-butyl 4-{[(2-bromo-4-chloro-5-methylphenyl)amino]carbonyl}piperidine-1-carboxylate 2-5 (2.90 g, 6.72 mmol) in N,N-dimethylformamide (40 mL) at approximately 0° C. The reaction mixture was warmed to ambient temperature and aged for 30 min. Benzyl bromide (1.20 mL, 10.1 mmol) was added and after 1 h, the reaction mixture was poured into aqueous 2 N hydrochloric acid and extracted with diethyl ether. The organic phase was washed with saturated aqueous sodium bicarbonate, brine, dried (sodium sulfate) and concentrated in vacuo to give a crude residue. Purification of the crude residue by flash chromatography over silica gel (gradient elution; 0%-20% acetone/methylene chloride as eluent) afforded 2-6 as a white solid.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with saturated aqueous sodium bicarbonate, brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. customto give a crude residue
  6. customPurification of the crude residue by flash chromatography over silica gel (gradient elution; 0%-20% acetone/methylene chloride as eluent)

Sources & evidence

ORD record
ord-5ee76dd5323f44c9a1f912ad74c1d50f
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07329673B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes