Water → HCID 10358222, compound

HRID 1681179Notes

Reaction equation

HRID 1681179 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.O>O1CCCC1>[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][O:17][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 736802(1-Benzylpiperidin-4-yl)methanol

Product 1

HCID 10358222HCID 10358222, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of sodium hydride (60% dispersion in oil, 0.76 g, 19 mmol) in anhydrous tetrahydrofuran (38 mL) was stirred at room temperature under a nitrogen atmosphere. A solution of 1-benzyl-4-hydroxymethyl piperidine (3.82 g, 18.6 mmol) was added dropwise. After the addition was completed, the reaction mixture was stirred for 2 h. 4-Fluorobenzyl bromide (2.4 mL, 19 mmol) was added dropwise, then the reaction mixture was stirred for 72 h. Water (50 mL) was added and the resulting mixture was extracted three times with ethyl acetate. Drying over magnesium sulfate, filtration and concentration in vacuo gave an oil. Vacuum distillation (170° C. (Kugelrohr oven), 1.0 Torr) gave a colorless oil (3.45 g, 59% yield): 'H-NMR: 7.34-6.98 (m, 9H), 4.46 (s, 2H), 3.50 (s, 2H), 2.93-2.87 (m, 2H), 2.02-1.59 (m, 5H), 1.39-125 HR-MS Calcd.: 313.1478; Found: 313.1479; (m, 2H); Anal. Calcd.: for C20H24FNO: C,76.65, H,7.72, N,4.47; Found: C,77.27, H,7.69, N,4.45.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for 2 h
  3. stirringthe reaction mixture was stirred for 72 h
  4. extractionthe resulting mixture was extracted three times with ethyl acetate
  5. dry with materialDrying over magnesium sulfate, filtration and concentration in vacuo
  6. customgave an oil
  7. distillationVacuum distillation (170° C. (Kugelrohr oven), 1.0 Torr)

Sources & evidence

ORD record
ord-7b6ba86995974316aa5f5feb10734bca
Source dataset
uspto-grants-1992_12
Patent number
US05169855

Reaction notes

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