Ammonia → 3-Methyl-7-phenyl-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole

HRID 267552

반응식

HRID 267552 반응식
[I-].[CH3:2][N+:3]12[CH2:18][CH2:17][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[NH:9][C:8]=3[C:7]1([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:6][CH2:5][CH2:4]2.[Li].COCC(O)C.N>C1C=CC=CC=1.CCCCCC>[CH3:2][N:3]1[CH2:4][CH2:5][CH2:6][CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]2[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:16]=2[CH2:17][CH2:18]1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 79001-Methoxy-2-propanolHCID 3028194LithiumHCID 215550172,3,5,6,11,11b-hexahydro-4-methyl-11b-phenyl-1H-indolizino[8,7-b]indolium iodide

생성물 1

HCID 215550043-Methyl-7-phenyl-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole

시약·촉매·용매 1

HCID 110624Benzene hexane용매

실험 절차

Then 2,3,5,6,11,11b-hexahydro-4-methyl-11b-phenyl-1H-indolizino[8,7-b]indolium iodide (8.09 g.), 286 mg. lithium, 2.03 g. 1-methoxy-2-propanol and 2 liters liquid ammonia are reacted according to the method of Example I-(a). The white foam isolated from the 1:9 and 1:4 benzene-hexane elutes is crystallized from hexane to provide 4.38 g. base. A 300 mg. portion is crystallized (twice) from hexane thereby yielding 200 mg. of title compound, m.p. 117°-119°C., NMR (CDCl3): δ 2.45 (singlet, 3-methyl), 5.70 (triplet, J 8 cps., 7-hydrogen) ppm.

후처리

  1. customis crystallized from hexane
  2. customto provide 4.38 g
  3. customportion is crystallized (twice) from hexane
  4. customthereby yielding 200 mg

출처 및 근거

ORD 기록
ord-e61c7fbdf936415a9c9ad3401aff2465
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03943148

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