Dimethylformamide → 2-[[1-(Phenylmethyl)-4-piperidinyl]oxy]pyridine

HRID 1087045Notes

Reaction equation

HRID 1087045 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.F[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.[H-].[Na+]>O>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 146789582-[[1-(Phenylmethyl)-4-piperidinyl]oxy]pyridineYield 106.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 60.65 H (318 mmoles) 1-phenylmethyl-4-piperidinol, 500 ml dimethylformamide, 46.25 g, that is 41 ml (475 mmoles) 2-fluoropyridine and 17 g 50% sodium hydride in mineral oil is heated at 100° C. for 1 h. The mixture is cooled in an ice bath, 20 ml water are added, the mixture is stirred for 30 min and concentrated to a residual volume of about 200 ml. 1 1 iced water is added, the mixture is stirred at 0° C. for 30 min, and the precipitate is filtered off, washed and dried. 90.71 g 1-phenylmethyl-4-(2-pyridinyloxy)piperidine are thus isolated. Melting point: 75° C.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. concentrationconcentrated to a residual volume of about 200 ml
  3. addition1 1 iced water is added
  4. stirringthe mixture is stirred at 0° C. for 30 min
  5. filtrationthe precipitate is filtered off
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-57e1146c77d344e5a8aa38b712de011a
Source dataset
uspto-grants-1991_07
Patent number
US05034401

Reaction notes

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