4-Fluorobenzonitrile → 4-(4-(Hydroxymethyl)piperidin-1-yl)benzonitrile

HRID 1757006Notes

Reaction equation

HRID 1757006 reaction equation
Cl.[OH:2][CH2:3][CH:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.F[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.C(N(C(C)C)C(C)C)C>>[C:15]([C:14]1[CH:17]=[CH:18][C:11]([N:7]2[CH2:8][CH2:9][CH:4]([CH2:3][OH:2])[CH2:5][CH2:6]2)=[CH:12][CH:13]=1)#[N:16]

Participants

4

Reactant 3

HCID 145174-FluorobenzonitrileHCID 81531DiisopropylethylamineHCID 24191744(Piperidin-4-yl)methanol--hydrogen chloride (1/1)

Product 1

HCID 193912964-(4-(Hydroxymethyl)piperidin-1-yl)benzonitrile

Procedure

A solution of 12.2 g of 4-hydroxymethyl-piperidine-hydrochloride, 9.8 g of 4-fluorobenzonitrile and 28.3 ml of N-ethyl-diisopropylamine is heated to 140° C. for 4 hours. After cooling, it is chromatographed over silica gel using methylene chloride and methylene chloride/ethyl acetate (1:1) as eluant. After the solvent has been removed under reduced pressure the residue remaining is triturated with petroleum ether and suction filtered. Yield: 5.1 g (29% of theory), Melting point: 148°-150° C.

Workup

  1. temperatureAfter cooling
  2. customit is chromatographed over silica gel
  3. customAfter the solvent has been removed under reduced pressure the residue
  4. customremaining is triturated with petroleum ether and suction
  5. filtrationfiltered

Sources & evidence

ORD record
ord-8c89c84550ef4a27a92cd3eab377674f
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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