Acetaldehyde → HCID 58993578, compound

HRID 391481Notes

Reaction equation

HRID 391481 reaction equation
[C:1]1([C:7]2([CH2:13][O:14][CH2:15][C:16]3[CH:17]=[C:18]([C:26]4[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=4)[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=3)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:34](=O)[CH3:35].C([BH3-])#N.[Na+]>C(#N)C.C(O)(=O)C>[CH2:34]([N:10]1[CH2:11][CH2:12][C:7]([CH2:13][O:14][CH2:15][C:16]2[CH:17]=[C:18]([C:26]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=3)[CH:19]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:21]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]1)[CH3:35]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 24785978HCID 24785978, compound

Product 1

HCID 58993578HCID 58993578, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

3′-(((4-phenylpiperidin-4-yl)methoxy)methyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (25.0 mg, 0.05 mmol) and acetaldehyde (0.25 mL, 4.31 mmol) were combined in acetonitrile (2.0 mL) and cooled to 0° C. The reaction was treated with sodium cyanoborohydride (14.0 mg, 0.23 mmol) and a few drops of acetic acid. The reaction was stirred at 0° C. for 30 min and at room temperature for 1 h. The solvent was removed in vacuo and the resulting crude mixture passed through a strong cation exchange column. After washing the column with several volumes of methanol, the product was eluted by washing the column with 2 M ammonia in methanol. The solvents were evaporated to afford 17 mg (79%). 1H-NMR (CDCl3, 500 MHz) δ 7.74-7.75 (m, 2H), 7.66 (s, 1H), 7.59-7.60 (m, 2H), 7.44 (s, 1H), 7.30-7.39 (m, 5H), 7.18-7.21 (m, 1H), 4.45 (s, 2H), 3.48 (s, 2H), 2.76 (s, 2H), 2.39-2.41 (m, 2H), 2.25-2.32 (m, 4H), 2.07-2.11 (m, 2H), 1.09 (t, J=7.0 Hz, 3H). 13C-NMR (CDCl3, 126 MHz) δ 144.0, 141.0, 140.1, 132.8, 131.7 (q, J=32.6 Hz), 129.0, 128.5, 128.0, 127.4, 126.3, 124.0 (q, J=272.6 Hz), 123.9, 123.0, 118.7, 111.9, 72.2, 52.5, 49.5, 41.4, 32.0, 11.8. Mass spec.: 479.15 (MH)+.

Workup

  1. customThe solvent was removed in vacuo
  2. washAfter washing the column with several volumes of methanol
  3. washthe product was eluted
  4. washby washing the column with 2 M ammonia in methanol
  5. customThe solvents were evaporated
  6. customto afford 17 mg (79%)

Sources & evidence

ORD record
ord-cc9a8cb4877b440c9ca62377e675f4ab
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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