Phenylacetaldehyde → HCID 67296383, compound

HRID 716771Notes

Reaction equation

HRID 716771 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:12])[CH2:9][C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1.[C:13]1([CH2:19][CH:20]=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+]>CO>[OH:12][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:3]=1)[CH2:9][C:10]#[N:11]

Participants

5

Reactant 3

HCID 998PhenylacetaldehydeHCID 4311764Sodium borohydrideHCID 593169603-(3-Aminophenyl)-3-hydroxypropanenitrile

Product 1

HCID 67296383HCID 67296383, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogenation of aniline 12 and 2-phenylacetaldehyde gives 3-hydroxy-3-(3-(phenethylamino)phenyl)propanenitrile. A mixture of aniline 12 (1.00 g, 6.17 mmol), 2-phenylacetaldehyde (0.66 g, 5.55 mmol) and A-3 molecular sieves in MeOH was stirred for 18 h and then NaBH4 (1.16 g, 30.8 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was filtered through Celite, concentrated under reduced pressure. Purification by column chromatography (100-200 silica mesh, 20% EtOAc—hexane) gave 3-hydroxy-3-(3-(phenethylamino)phenyl)propanenitrile as a yellow liquid. Yield (0.432 g, 27%); 1H NMR (400 MHz, DMSO-d6) δ 7.32-7.26 (m, 4H), 7.20 (t, J=6.4 Hz, 1H), 7.04 (t, J=7.6 Hz, 1H), 6.64 (s, 1H), 6.55 (d, J=7.2 Hz, 1H), 6.50 (d, J=8.4 Hz, 1H), 5.77 (d, J=4.4 Hz, 1H), 5.68 (t, J=5.6 Hz, 1H), 4.76-4.72 (m, 1H), 3.26-3.21 (m, 2H), 2.85-2.81 (m, 3H), 2.79-2.72 (m, 1H).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. customPurification by column chromatography (100-200 silica mesh, 20% EtOAc—hexane)

Sources & evidence

ORD record
ord-f5c8461809fd4c9385faf7ca4a342917
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

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