2,2-Dipropyloxirane → 3-Hydroxy-3-(3-(2-hydroxy-2-propylpentylamino)phenyl)propanenitrile

HRID 716772Notes

Reaction equation

HRID 716772 reaction equation
[CH2:1]([C:4]1([CH2:7][CH2:8][CH3:9])[CH2:6][O:5]1)[CH2:2][CH3:3].[NH2:10][C:11]1[CH:12]=[C:13]([CH:17]([OH:21])[CH2:18][C:19]#[N:20])[CH:14]=[CH:15][CH:16]=1>>[OH:21][CH:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([NH:10][CH2:6][C:4]([OH:5])([CH2:7][CH2:8][CH3:9])[CH2:1][CH2:2][CH3:3])[CH:12]=1)[CH2:18][C:19]#[N:20]

Participants

3

Reactant 2

HCID 134110112,2-DipropyloxiraneHCID 593169603-(3-Aminophenyl)-3-hydroxypropanenitrile

Product 1

HCID 672964943-Hydroxy-3-(3-(2-hydroxy-2-propylpentylamino)phenyl)propanenitrile

Procedure

Reaction between 2,2-dipropyloxirane and aniline 12 gave 3-hydroxy-3-(3-(2-hydroxy-2-propylpentylamino)phenyl)propanenitrile as a pale yellow semi-solid. Yield (1.0 g, 40%); 1H NMR (400 MHz, CDCl3) δ 7.17 (t, J=8.0 Hz, 1H), 6.69-6.67 (m, 2H), 6.63 (d, J=8.0 Hz, 1H), 4.96-4.94 (m, 1H), 4.05 (bs, 1H), 3.08 (s, 2H), 2.76 (d, J=6.4 Hz, 2H), 2.36 (bs, 1H), 1.52 (t, J=8.4 Hz, 4H), 1.41-1.32 (m, 4H), 0.94 (t, J=7.2 Hz, 6H).

Sources & evidence

ORD record
ord-6fc2fd02c258431292aa52f2e3e4f1cf
Source dataset
uspto-grants-2015_11
Patent number
US09193669B2

Reaction notes

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