Ammonium formate → 4-(4-Propylmorpholin-2-yl)phenol

HRID 600229Notes

Reaction equation

HRID 600229 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:20][CH2:19][CH2:18][N:17]([CH2:21][CH2:22][CH3:23])[CH2:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:21]([N:17]1[CH2:18][CH2:19][O:20][CH:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH2:16]1)[CH2:22][CH3:23]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 574406922-(4-Benzyloxyphenyl)-4-propylmorpholine

Product 1

HCID 444439424-(4-Propylmorpholin-2-yl)phenolYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl ether from example 28 (3.0 g, 9.64 mmol) was dissolved in methanol (150 ml) and 10% palladium on charcoal (800 mg) was added. The reaction mixture was stirred for a few minutes before ammonium formate (6.17 g, 96.4 mmol) was added portionwise. The reaction mixture was carefully heated to 80° C. until gas evolution had ceased. After cooling, the reaction mixture was filtered through arbacel, washed with methanol (50 ml) and concentrated in vacuo to give the title compound as a white crystalline solid (1.51 g, 6.83 mmol, 71%). 1H NMR (CDCl3, 400 MHz) δ: 0.91 (t, 3H), 1.58 (q, 2H), 2.10 (t, 1H), 2.22 (t, 1H), 2.40 (dd, 2H), 2.81 (d, 1H), 2.93 (d, 1H), 3.85 (t, 1H), 4.02 (dd, 1H), 4.57 (d, 1H), 6.79 (d, 2H), 7.21 (d, 2H). LRMS: m/z 222 (M-H+).

Workup

  1. additionwas added portionwise
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered through arbacel
  4. washwashed with methanol (50 ml)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67ddec32e29b41e7ad35ba12f3d6d592
Source dataset
uspto-grants-2011_03
Patent number
US07902188B2

Reaction notes

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