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

HRID 899109ノート

反応式

HRID 899109 の反応式
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]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 69291610HCID 69291610、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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”

出典と根拠

ORDレコード
ord-cd1e55b6b92f4291a04a64773add8760
出典データセット
uspto-grants-2008_04
特許番号
US07354920B2

反応ノート

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