Dimethylcarbamoyl Chloride → HCID 118037408, compound

HRID 715561Notes

Reaction equation

HRID 715561 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:17][N:18]([CH3:22])[C:19](Cl)=[O:20]>O1CCCC1>[CH3:17][N:18]([CH3:22])[C:19](=[O:20])[O:14][CH:11]1[CH2:10][CH2:9][N:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydrideHCID 235052161-(4-Bromophenyl)piperidin-4-ol

Product 1

HCID 118037408HCID 118037408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Bromophenyl)piperidin-4-ol (200 mg) is dissolved under argon in tetrahydrofurane (4 mL), cooled to 0° C. and treated with NaH (60% in mineral oil, 36 mg). The mixture is stirred for 30 minutes, treated with dropwise with dimethylcarbamoylchloride (110 μL) and stirred for 4 hours at room temperature. Then the mixture is partitioned between water and ethylacetate. The organic phase is washed with water and brine and is dried (MgSO4). The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50) to give the title compound. LC (method 3): tR=1.05 min; Mass spectrum (ESI+): m/z=327 [M+H]+.

Workup

  1. stirringstirred for 4 hours at room temperature
  2. customThen the mixture is partitioned between water and ethylacetate
  3. washThe organic phase is washed with water and brine
  4. dry with materialis dried (MgSO4)
  5. customThe solvents are evaporated in vacuo
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→50:50)

Sources & evidence

ORD record
ord-00dab08fa5e948f5950c1f99c6498ddd
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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