Ammonium formate → 2-(2,6-Dichloro-phenyl)-1-morpholin-2-yl-1-phenyl-ethanol hydrochloride

HRID 899109Notes

Reaction equation

HRID 899109 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([OH:24])[CH2:15][C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[ClH:22].[Cl:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:23])[C:16]=1[CH2:15][C:14]([CH:10]1[O:11][CH2:12][CH2:13][NH:8][CH2:9]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[OH:24]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69291610HCID 69291610, compound

Product 1

HCID 692921202-(2,6-Dichloro-phenyl)-1-morpholin-2-yl-1-phenyl-ethanol hydrochlorideYield 30.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-Benzyl-morpholin-2-yl)-2-(2,6-dichloro-phenyl)-1-phenyl-ethanol (450 mg, 1 equiv.) in ethyl acetate (15 mL) at room temperature under nitrogen atmosphere was added ammonium formate (1.69 g, 25 equiv.) followed by addition of palladium on charcoal (10%, 45 mg.). The reaction mixture was heated to reflux for 3 hour, cooled to room temperature and then filtered through Celite. All volatiles were evaporated under vacuum, and the resulting solid was purified via preparative HPLC. The isolated white solid was taken up in ethanol. Hydrogen chloride was added (large excess of 2M solution in diethyl ether) and the mixture was stirred until it became a clear solution. Then all the volatiles were evaporated “in vacuo”, to give 60 mg of the title compound as white solid. 1H NMR (300M1, CD3OD D4) δ: 2.52-2.61 (d, 1H), 2.79-2.96 (t, 1H), 2.98-3.13 (t, 1H), 3.15-3.19 (s, 1H), 3.56-3.71 (q, 2H), 3.88-4.02 (t, 1H), 4.10-4.21 (d, 1H), 4.29-4.39 (d, 1H), 6.97-7.08 (m, 1H), 7.10-7.21 (m, 7H). LCMS (12 minutes method) [M+H]+=352 @ Rt 4.63 min. single major peak.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hour
  3. filtrationfiltered through Celite
  4. customAll volatiles were evaporated under vacuum
  5. customthe resulting solid was purified via preparative HPLC
  6. additionHydrogen chloride was added (large excess of 2M solution in diethyl ether)
  7. customThen all the volatiles were evaporated “in vacuo”

Sources & evidence

ORD record
ord-cd1e55b6b92f4291a04a64773add8760
Source dataset
uspto-grants-2008_04
Patent number
US07354920B2

Reaction notes

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