1-Bromohexane → HCID 23001070, compound

HRID 397745Notes

Reaction equation

HRID 397745 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])O.[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CN(C)C=O>[CH2:21]([N:11]1[CH2:12][CH2:13][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=2)([CH3:14])[CH2:9][CH2:10]1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 516892Sodium BicarbonateHCID 22707892HCID 22707892, compound

Product 1

HCID 23001070HCID 23001070, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 4-(3-hydroxyphenyl)-4-methylpiperidine (776 mg, 4.06 mmol) in N,N-dimethylformamide (5 ml) was added sodium hydrogen carbonate (341 mg, 4.06 mmol) and 1-bromohexane (0.57 ml, 4.06 mmol). The reaction mixture was heated at 100° C. for 4 h and then allowed to cool to room temperature. The solution was poured onto water (20 ml) and extracted with diethyl ether (3×10 ml). The combined extracts were washed with water (20 ml), dried (MgSO4) and concentrated in vacuo to give the title compound as a clear oil (1.0 g, 90%).

Workup

  1. temperatureto cool to room temperature
  2. additionThe solution was poured onto water (20 ml)
  3. extractionextracted with diethyl ether (3×10 ml)
  4. washThe combined extracts were washed with water (20 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d49a58afd6f4288aceb84096da13762
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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