Hydrochloric Acid → 1,4'-Bipiperidin-4-ol

HRID 1060820

반응식

HRID 1060820 반응식
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=O)(C)(C)C.OC1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClC(Cl)C.CO.C(O)(=O)C>[N:8]1([CH:6]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 79341Piperidin-4-olHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 220613421,4'-Bipiperidin-4-ol

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 63651,1-Dichloroethane용매

실험 절차

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (20 g) and 4-hydroxypiperidine (6.7 g) were stirred together in dichloroethane (200 ml) with acetic acid (4 ml) at RT for 30 minutes. Sodium triacetoxyborohydride (23 g) was then added and the mixture stirred at RT overnight. The mixture was evaporated to dryness and the residue taken into water, extracted with diethyl ether (3×200 ml), the aqueous was basified to pH 9-10 and extracted with dichloromethane (3×200 ml). The dichloromethane extracts were combined, dried (MgSO4) and evaporated to leave an oil (19 g; same compound as Example 9 step 1). The oil was dissolved in methanol (300 ml) and treated with concentrated hydrochloric acid (5 ml). The mixture was stirred overnight and then evaporated to dryness to leave the title compound as the hydrochloride salt (15 g).

후처리

  1. customThe mixture was evaporated to dryness
  2. extractionextracted with diethyl ether (3×200 ml)
  3. extractionextracted with dichloromethane (3×200 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto leave an oil (19 g; same compound as Example 9 step 1)
  7. stirringThe mixture was stirred overnight
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-ce78c81427db4a43bfe750158d2f3136
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525070B2

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