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

HRID 1900250

反応式

HRID 1900250 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Dissolved 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-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.

後処理

  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

出典と根拠

ORDレコード
ord-19a91169cece42e8b3db6a59a930f340
出典データセット
uspto-grants-1996_11
特許番号
US05574173

関連ノート

読み込み中…