Water → HCID 69006529, compound

HRID 1725582Notes

Reaction equation

HRID 1725582 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:6][C:7](=[CH:10][N:11]1[CH2:16][CH2:15]OCC1)[C:8]#[N:9].Cl.N[C:32]1[CH:37]=CC=[CH:34][CH:33]=1.O>C(O)(C)C>[NH:11]([CH:10]=[C:7]([CH2:6][C:5]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[C:3]([O:2][CH3:1])[CH:4]=1)[C:8]#[N:9])[C:16]1[CH:34]=[CH:33][CH:32]=[CH:37][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8870Benzenamine hydrochloride (1:1)HCID 86590609HCID 86590609, compound

Product 1

HCID 69006529HCID 69006529, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a homogeneous solution of 2-{3-methoxy-4-[(4-methoxybenzyl)oxy]benzyl}-3-morpholin-4-ylprop-2-enenitrile (14.5 g, 36.7 mmol) in isopropanol (050 mL) was added aniline hydrochloride (4.9 g, 37.5 mmol), and the mixture was stirred at reflux for 20 minutes, combined with 20 mL of water and cooled in an ice bath for 30 minutes. The resulting precipitate was filtered off, washed with water and air dried to give 13.7 g of crude product. This material was recrystalized from methanol/ethanol to afford pure product as a crystalline tan solid (10.5 g, 26.2 mmol). 1H NMR (300 MHz, d6-DMSO): δ 9.03 (d, J=12.8 Hz, 1H), 7.59 (d, J=12.8 Hz, 1H), 7.30 (d, J=8.6 Hz, 2H), 7.20 (d, J=7.4 Hz, 2H), 7.16 (m,2H), 6.93 (d, J=8.2 Hz, 1H), 6.88 (d, J=8.4, 1H), 6.86 (m, 1H), 6.83 (s, 1H), 4.90 (s, 2H), 3.69 (s, 3H), 3.68 (s, 3H), 3.50 (s, 2H), 3.28 (s, 2H). MS (ES-, m/z)=399 (M−H).

Workup

  1. temperatureat reflux for 20 minutes
  2. temperaturecooled in an ice bath for 30 minutes
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water and air
  5. customdried
  6. customto give 13.7 g of crude product
  7. customThis material was recrystalized from methanol/ethanol

Sources & evidence

ORD record
ord-bfdc9b9492994a549f9666a036ffad13
Source dataset
uspto-grants-2009_02
Patent number
US07491731B2

Reaction notes

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