p-Toluenesulfonic acid → 4-(1-Benzylpiperidin-4-yl)morpholine

HRID 661598

반응식

HRID 661598 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.C(O)(=O)C>[C:2]1([CH2:1][N:8]2[CH2:13][CH2:12][CH:11]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 5

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 51700761-Benzyl-2-piperidone

생성물 1

HCID 7838314-(1-Benzylpiperidin-4-yl)morpholine

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

30 mL (0.162 Mol) 1-benzylpiperidone (L) and 16.1 mL (0.185 Mol) morpholine (M) are dissolved in 407 mL tetrahydrofuran at ambient temperature. While cooling, 1.0 g (5 mmol) of p-toluenesulphonic acid and 14.6 mL glacial acetic acid are added, whereupon a jelly-like precipitate is formed. 52.19 g (0.246 Mol) sodium triacetoxyborohydride are added while cooling with ice, during which time the reaction temperature rises to 30° C. After 4 hours at 20° C., 90 mL water are added dropwise. After another 30 minutes, 280 mL of 17% potassium carbonate solution are added. The mixture is stirred intensively, while gas is observed to be given off. After separation of the phases the organic phase is dried and evaporated down.

후처리

  1. temperatureWhile cooling
  2. customis formed
  3. temperaturewhile cooling with ice, during which time the reaction temperature
  4. customrises to 30° C
  5. waitAfter another 30 minutes
  6. customAfter separation of the phases the organic phase
  7. customis dried
  8. customevaporated down

출처 및 근거

ORD 기록
ord-0d55e187f0a140e6a5d84707a7c61774
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084634B2

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