4-Amino-1-Boc-piperidine → HCID 67188470, compound

HRID 545640Notes

Reaction equation

HRID 545640 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[NH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]2)=[C:6]([C:7]#[N:8])[CH:9]=1

Participants

4

Reactant 2

HCID 12682914-Amino-1-Boc-piperidineHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 67188470HCID 67188470, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

5-bromo-2-fluorobenzonitrile (2.00 g, 10.00 mmol) and tert-butyl 4-aminopiperidine-1-carboxylate (5.01 g, 25.0 mmol) were dissolved in a minimal amount of chloroform (3 ml) and heated at 110° C. for 20 h, during which all of the solvent evaporated. The resulting crude golden yellow oil was taken up in CH2Cl2 and washed with saturated aqueous NaHCO3 and brine, and dried (MgSO4). Flash chromatography with 25:10:65 and 35:10:55 EtOAc-CH2Cl2-Hexane of the concentrated organic layers gave the desired product, tert-butyl 4-(4-bromo-2-cyanophenylamino)piperidine-1-carboxylate as a light yellow glassy foam. MS m/e 379.1 (M−H)−.

Workup

  1. customevaporated
  2. washwashed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-9ad47d842409487bbdcbc382fe4f9b84
Source dataset
uspto-grants-2011_05
Patent number
US07935709B2

Reaction notes

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