2-Bromo-4'-methylacetophenone → HCID 68566507, compound

HRID 1867582Notes

Reaction equation

HRID 1867582 reaction equation
C([O-])(=O)C.[Na+].[NH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)=O.[O-:31][C:32]#[N:33].[Na+]>C(#N)C.O.C(O)(=O)C>[CH3:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]2[NH:33][C:32](=[O:31])[N:6]([CH:7]3[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]3)[CH:21]=2)=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 692722-Bromo-4'-methylacetophenoneHCID 517045Sodium AcetateHCID 517096Sodium CyanateHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 68566507HCID 68566507, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

Sodium acetate (41 mg, 0.50 mmol) was added to a solution of t-butyl 4-aminopiperidine-1-carboxylate (100 mg, 0.50 mmol) in acetonitrile (2 mL) at 0° C. After 5 min, 2-bromo-4′-methylacetophenone (106.4 mg, 0.50 mmol) in acetonitrile (1 mL) was added and the mixture was allowed to warm to ambient temperature. After 1.5 h, sodium cyanate (97.4 mg, 1.5 mmol), acetic acid (100 uL) and water (80 uL) were added to the reaction mixture. After 16 h, the mixture was concentrated to give the title compound.

Workup

  1. waitAfter 1.5 h
  2. waitAfter 16 h
  3. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-cf45ca9c374645d1a08b78381f027da3
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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