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Sodium Iodide → (3-(4-Cyano-4-(2,4-difluorophenyl)piperidin-1-yl)propyl)carbamic acid tert-butyl ester

HRID 1066996
Notes
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Reaction equation

HRID 1066996 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:15]#[N:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[C:17]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27]Br)=[O:23])([CH3:20])([CH3:19])[CH3:18].[I-].[Na+]>CC(C)=O>[C:17]([O:21][C:22](=[O:23])[NH:24][CH2:25][CH2:26][CH2:27][N:12]1[CH2:13][CH2:14][C:9]([C:15]#[N:16])([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH2:10][CH2:11]1)([CH3:20])([CH3:19])[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 105132084-(2,4-Difluorophenyl)-piperidine-4-carbonitrile

Product 1

HCID 18353383(3-(4-Cyano-4-(2,4-difluorophenyl)piperidin-1-yl)propyl)carbamic acid tert-butyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 180Acetone
Solvent

Procedure

To a stirred solution of 4-(2,4-difluorophenyl)-piperidine-4-carbonitrile (0.203 g, 0.914 mmol) in acetone (20 ml), N-(tert-butoxycarbonyl)-3-bromopropylamine (0.239 g, 1.00 mmol) potassium carbonate (0.505 g, 3.65 mmol) and sodium iodide (0.274 g, 1.82 mmol) were added and the solution refluxed for 24 hours. The reaction mixture was cooled to room temperature, concentrated and partitioned between chloroform (20 mL) and water (5 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (ethyl acetate) to yield 0.259 g (75%) of the required product as a colorless oil.

Workup

  1. temperaturethe solution refluxed for 24 hours
  2. concentrationconcentrated
  3. custompartitioned between chloroform (20 mL) and water (5 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-3cdfd36220b54f46bd16fa66b72d0afd
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06245773B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes