Ammonium formate → 4-[(1-Azetidin-3-ylpiperidin-4-yl)carbonyl]morpholine

HRID 426092ノート

反応式

HRID 426092 の反応式
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[O:19])[CH2:14][CH2:13]3)[CH2:9]2)C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:9][CH:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[O:19])[CH2:14][CH2:13]2)[CH2:11]1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 236589584-({1-[1-(Diphenylmethyl)azetidin-3-yl]piperidin-4-yl}carbonyl)morpholine

生成物 1

HCID 236589574-[(1-Azetidin-3-ylpiperidin-4-yl)carbonyl]morpholine収率 43.4%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

反応条件

温度
120 °C

実験手順

4-({1-[1-(Diphenylmethyl)azetidin-3-yl]piperidin-4-yl}carbonyl)morpholine (0.44 g, 1.0 mmol) was dissolved in ethanol and to the resultant solution was added palladium hydroxide on carbon (0.15 g) and ammonium formate (0.27 g, 4.2 mmol). The reaction mixture was heated for 2 min at 120° C. using microwave single node heating. The catalyst was filtered off by means of a phase separator and the filter cake washed with ethanol. The solvent was removed by evaporation and the residue was dissolved in methanol (1 mL) and THF (10 mL). The solution was loaded on a cation exchange sorbent (Isolute® SCX-2; 10 g). The column washed with THF and the product was then eluted with ammonia saturated methanol. The solvent of the collected fractions was removed by evaporation and there was obtained 0.11 g of the title compound as colourless oil. 1H NMR (500 MHz, CD3OD): 1.7-1.8 (m, 4H), 1.9-2.0 (m, 2H), 2.6-2.9 (m, 4H), 3.3-3.4 (m, 1H), 3.5-3.7 (m, 8H), 3.8-4.0 (m, 3H); LCMS: m/z 254 (M+1)+.

後処理

  1. temperatureheating
  2. filtrationThe catalyst was filtered off by means of a phase separator
  3. washthe filter cake washed with ethanol
  4. customThe solvent was removed by evaporation
  5. dissolutionthe residue was dissolved in methanol (1 mL)
  6. washThe column washed with THF
  7. washthe product was then eluted with ammonia saturated methanol
  8. customThe solvent of the collected fractions was removed by evaporation

出典と根拠

ORDレコード
ord-d873ece4845a454183594df8097b4145
出典データセット
uspto-grants-2012_01
特許番号
US08106208B2

反応ノート

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