Ether hydrochloride → (4-fluoropiperidin-4-yl)Methanol hydrochloride

HRID 1035253Notes

Reaction equation

HRID 1035253 reaction equation
[F:1][C:2]1([CH2:15][OH:16])[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.[ClH:17].CCOCC>CCOCC>[ClH:17].[F:1][C:2]1([CH2:15][OH:16])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 22248400tert-Butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 56971709(4-fluoropiperidin-4-yl)Methanol hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of tert-butyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (21 g, 0.09 mol) in dry ether (200 mL) was added HCl/ether (4M, 100 mL) drop-wise at 0° C. under N2. After addition, the mixture was allowed to warm to RT and stirred overnight. The reaction mixture was concentrated to remove solvent and the residue was washed with ether. 1H NMR (400 MHz, D2O): δ 1.78 (m, 2H), 2.05 (m, 2H), 3.15 (m, 2H), 3.31 (m, 2H), 3.57 (d, 2H), m/z 134 [M+H]+.

Workup

  1. additionAfter addition
  2. concentrationThe reaction mixture was concentrated
  3. customto remove solvent
  4. washthe residue was washed with ether

Sources & evidence

ORD record
ord-7719af042e154a458da055977fb3e6d7
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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