Benzaldehyde → 3-(3-(Benzylamino)phenyl)-3-hydroxypropanenitrile

HRID 716792Notes

Reaction equation

HRID 716792 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]([OH:26])[CH2:23][C:24]#[N:25])[CH:19]=[CH:20][CH:21]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:27]([NH:15][C:16]1[CH:17]=[C:18]([CH:22]([OH:26])[CH2:23][C:24]#[N:25])[CH:19]=[CH:20][CH:21]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 593169603-(3-Aminophenyl)-3-hydroxypropanenitrile

Product 1

HCID 672967283-(3-(Benzylamino)phenyl)-3-hydroxypropanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaBH(OAc)3 (7.84 g, 36.99 mmol) was added to a solution of aniline 12 (2.0 g, 12.33 mmol) and benzaldehyde (1.3 g, 12.33 mmol) in DCM. The resulting mixture was stirred at RT for 5 h and quenched with saturated aqueous NaHCO3. Organic layer was washed with water followed by brine and dried over anhydrous Na2SO4. Organic layer was concentrated under reduced pressure. Purification by flash chromatography (40% to 50% EtOAc—hexanes gradient) gave 3-(3-(benzylamino)phenyl)-3-hydroxypropanenitrile as a pale yellow oil. Yield (2.61 g, 83%); 1H NMR (400 MHz, DMSO-d6) δ 7.36-7.29 (m, 4H), 7.23-7.19 (m, 1H), 6.99 (t, J=8.0 Hz, 1H), 6.68 (s, 1H), 6.54 (d, J=7.6 Hz, 1H), 6.44 (dd, J=1.6, 8.0 Hz, 1H), 6.27 (t, J=6.0 Hz, 1H), 5.79 (d, J=4.4 Hz, 1H), 4.72-4.68 (m, 1H), 4.25 (d, J=6.0 Hz, 2H), 2.82-2.67 (m, 2H).

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. washOrganic layer was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationOrganic layer was concentrated under reduced pressure
  5. customPurification by flash chromatography (40% to 50% EtOAc—hexanes gradient)

Sources & evidence

ORD record
ord-06dbc9892d76453b8558a4eaaa315c1b
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

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