Acetonitrile → (1-(4-Nitrophenyl)piperidin-4-yl)methanol

HRID 1261888Notes

Reaction equation

HRID 1261888 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([N:6]2[CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4][CH2:5]2)=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 4207714-Piperidinemethanol

Product 1

HCID 23448266(1-(4-Nitrophenyl)piperidin-4-yl)methanolYield 78%

Conditions

Temperature
60 °C

Procedure

Into a 1-Neck round-bottom flask 4-(Hydroxymethyl)piperidine (6.53 g, 56.7 mmol), Potassium carbonate (7.84 g, 56.7 mmol), Acetonitrile (50 mL, 1000 mmol), and [A] 4-Fluoronitrobenzene (4.00 g, 28.3 mmol)were added. The reaction was heated at 60° C. overnight. The reaction content was poured into ice water and stirred for 30 minutes. The solid was filtered, washed with water and dried under vacuum to give [1-(4-Nitro-phenyl)-piperidin-4-yl]-methanol as an off-white solid (5.20 g, 78%). NMR 1H (DSMO-d6)-8.02 (d, 2H, J=9.40 Hz), 7.00 (d, 2H J=9.49 Hz), 4.50 (bs, 1H), 4.07 (bd, 1H, J=13.33 Hz), 3.27 (d, 1H, J=5.84 Hz), 2.94 (t, 2H), 1.80-1.95 (m, 3H), 1.02-1.13 (m, 2H)

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d7adb207d9334d09a559989dbca0bb70
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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