1-Bromohexane → HCID 23000911, compound

HRID 397754Notes

Reaction equation

HRID 397754 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][CH2:15][CH3:16])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])O.[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C)C=O.O>[NH3:11].[CH2:23]([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)([CH2:14][CH2:15][CH3:16])[CH2:9][CH2:10]1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 3

HCID 81011-BromohexaneHCID 516892Sodium BicarbonateHCID 23000993HCID 23000993, compound

Product 2

HCID 222AmmoniaHCID 23000911HCID 23000911, compoundYield 154.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 4-(3-hydroxyphenyl)-4-n-propylpiperidine (Preparation 67, 1.10 g, 5.0 mmol) in N,N-dimethylformamide (25 ml) was added sodium hydrogen carbonate (462 mg, 5.5 mmol) and 1-bromohexane (0.77 ml, 5.5 mmol). The reaction mixture was heated at 100° C. for 3 h 30 min and then allowed to cool to room temperature. The mixture was diluted with water (25 ml) and extracted with dichloromethane (3×25 ml). The combined extracts were washed with water (20 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by (50 g) silica column chromatography eluting with ethyl acetate:hexane:0.880 ammonia (40:60:1) to give the title compound as a pale yellow oil (1.17 g, 77%).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with dichloromethane (3×25 ml)
  3. washThe combined extracts were washed with water (20 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by (50 g) silica column chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-69e16e14a2cf47ea8bad28c265d39bfb
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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