Methanol → 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1-methyl-1,2,5,6-tetrahydropyridine

HRID 128640

반응식

HRID 128640 반응식
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CO>C1COCC1>[CH:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([C:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH:17]=3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 1688974-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidineHCID 178418339Butyllithium

생성물 1

HCID 214741334-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1-methyl-1,2,5,6-tetrahydropyridine수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Dissolved 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-methylpiperidine (12 g, 0.042 mol) in 250 mL of dry THF. Cooled to -78° C. under a nitrogen atmosphere. Added n-butyl lithium (18 mL of 2.5M in hexane) dropwise via addition funnel. Maintain temperature at 0° C. for 1 hour then recooled to -78° C. Added 21 mL of dry methanol, and let warm to room temperature. Added saturated NH4Cl, and extracted with THF. Dried combined organic extracts with MgSO4, filtered, and evaporated to give 11.3 g (94% yield) of 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1-methyl-1,2,5,6-tetrahydropyridine as a white solid.

후처리

  1. temperatureMaintain temperature at 0° C. for 1 hour
  2. customthen recooled to -78° C
  3. temperaturelet warm to room temperature
  4. extractionAdded saturated NH4Cl, and extracted with THF
  5. customDried
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-89450fb617134dd285a57e7b2cda92bb
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464840

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