1-Benzylpiperidine-4-carbaldehyde → Hydroxy[1-(phenylmethyl)-4-piperidinyl]acetonitrile

HRID 1787701Notes

Reaction equation

HRID 1787701 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al]([C:21]#[N:22])(CC)CC>C1COCC1>[OH:15][CH:14]([CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1)[C:21]#[N:22]

Participants

4

Reactant 2

HCID 895841-Benzylpiperidine-4-carbaldehydeHCID 16683962(cyano-C)diethylaluminium

Product 1

HCID 57599582Hydroxy[1-(phenylmethyl)-4-piperidinyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(phenylmethyl)-4-piperidinecarbaldehyde (2.35 g, 11.6 mmol)[prepared according to Alfaro-Lopez, J.; et al. J. Med. Chem. 1999, 42, 5359] in THF (160 mL) at 0° C. was added dropwise Et2AlCN (25 mL, 1 M solution in toluene). After 1 h, the solution was partitioned between NaHCO3(sat)-DCM. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried (Na2SO4) and concentrated yielding the title compound as a yellow oil which was used directly without further purification: LCMS (ES) m/e 249 (M+H)+.

Workup

  1. customthe solution was partitioned between NaHCO3(sat)-DCM
  2. extractionThe aqueous phase was extracted several times with DCM
  3. dry with materialthe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-de5b0b3700db4aca811d49ebfe56129e
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

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