Triethylamine → 1-Oxa-3,8-diazaspiro(4.5)decan-2-one, 8-benzyl-

HRID 565608

반응식

HRID 565608 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:16])([CH2:14][NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24](Cl)(Cl)=[O:25].C1(C)C=CC=CC=1>C(#N)C.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([O:16][C:24](=[O:25])[NH:15][CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 104210264-(Aminomethyl)-1-benzylpiperidin-4-olHCID 19083224Phosgen toluene

생성물 1

HCID 1998151-Oxa-3,8-diazaspiro(4.5)decan-2-one, 8-benzyl-

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of crude 1-benzyl-4-hydroxy-4-aminomethyl piperidine, as described above in Step A, (˜3.1 gm, 12 mmol) in acetonitrile (50 mL) containing triethyl amine (5.7 mL, 42 mmol) cooled in an ice bath was added in 1 mL portions 20% phosgene/toluene (9 mL) over a three hour period. The reaction mixture was stirred at ambient temp. for 15 hours and diluted with ethyl acetate. This solution was washed with water (2×) and the organic layer dried (anhyd. sodium sulfate), filtered, and the solvent removed under vacuum. The residue was triturated with diethyl ether and the title compound collected by filtration as a white solid, mp: 159-161° C.

후처리

  1. temperaturecooled in an ice bath
  2. washThis solution was washed with water (2×)
  3. dry with materialthe organic layer dried (anhyd. sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent removed under vacuum
  6. customThe residue was triturated with diethyl ether
  7. filtrationthe title compound collected by filtration as a white solid, mp: 159-161° C.

출처 및 근거

ORD 기록
ord-52baa319d75b4b72b9b4abc10cab7d1f
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172076B2

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