HCID 46926628, compound → 4-(3-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)propoxy)benzonitrile

HRID 1503344Notes

Reaction equation

HRID 1503344 reaction equation
[C:1]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([Mg]Br)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[OH:8][C:1]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 46926628HCID 46926628, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 445437004-(3-(4-(Hydroxydiphenylmethyl)piperidin-1-yl)propoxy)benzonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(3-(4-Benzoylpiperidin-1-yl)propoxy)benzonitrile (0.5 g, 1.4 mmol) was dissolved in dry THF (˜15 mL), and a solution of phenylmagnesium bromide (0.9 mL, 2M, 1.8 mmol) was added and the reaction stirred for 6 h. The reaction was quenched (sat. NH4Cl) and extracted into EtOAc (2×). The organic layers were dried over Na2SO4 and the volatiles removed under reduced pressure. The crude residue was purified on silica gel (EtOAc/hexanes) to give 417 mg (70% yield) of title compound Example B1: 1H NMR (400 MHz, CDCl3) δ 7.58 (2H, d, J=8.8 Hz), 7.50 (4H, d, J=7.6), 7.30 (4H, q, J=8), 7.20 (2H, t, J=7.2 Hz), 6.94 (2H, d, J=8.8 Hz), 4.06 (2H, t, J=6 Hz), 3.07 (2H, d, J=11.2 Hz), 2.59 (2H, t, J=7.2 Hz), 2.53-2.46 (1H, m), 2.14-2.01 (4H, m), 1.66-1.55 (4H, m), LC-MS (>98%) m/z=427.0 [M+H]; HRMS=427.2386 [M+H], 100% calculated for C28H31N2O2, 427.2386.

Workup

  1. customThe reaction was quenched (sat. NH4Cl)
  2. extractionextracted into EtOAc (2×)
  3. dry with materialThe organic layers were dried over Na2SO4
  4. customthe volatiles removed under reduced pressure
  5. customThe crude residue was purified on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-410988c93940470191d61635159afbc1
Source dataset
uspto-grants-2015_12
Patent number
US09212180B2

Reaction notes

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