Hydrochloric Acid → 4-{[3-(3,8-Diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile

HRID 1743708ノート

反応式

HRID 1743708 の反応式
C([N:8]1[CH2:14][CH:13]2[N:15]([CH2:16][CH2:17][CH2:18][NH:19][C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)C1C=CC=CC=1.Cl.C(Cl)Cl>C(#N)C>[CH:10]12[N:15]([CH2:16][CH2:17][CH2:18][NH:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=3)[CH:13]([CH2:12][CH2:11]1)[CH2:14][NH:8][CH2:9]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 222354174-{[3-(3-Benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile

生成物 1

HCID 222354684-{[3-(3,8-Diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile収率 43%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a cold solution of 4-{[3-(3-benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)propyl]amino}benzonitrile (6.26 g, 17.4 mmol; from step (c) above) in acetonitrile (100 mL) was added 12 M HCl (5.8 mL). The reaction mixture was stirred for 15 minutes, concentrated in vacuo and dried under high vacuum overnight. The resulting hydrochloride salt was added to a suspension of 10% Pd/C (800 mg) in methanol (250 mL). The reaction was then stirred under hydrogen (1 atmosphere of pressure) for 50 min. The mixture was filtered through Celite® and the filtrate was concentrated in vacuo. The resulting residue was partitioned with saturated NaHCO3 (100 mL) and CH2Cl2 (200 mL). The organic layer was dried (Na2SO4), filtered and concentrated ill vacuo to give the crude product. Flash chromatography on silica gel eluting with a gradient of CH2Cl2:CMA (4:1 to 2:1) gave 2.02 g (43%) of the title compound.

後処理

  1. concentrationconcentrated in vacuo
  2. customdried under high vacuum overnight
  3. additionThe resulting hydrochloride salt was added to a suspension of 10% Pd/C (800 mg) in methanol (250 mL)
  4. stirringThe reaction was then stirred under hydrogen (1 atmosphere of pressure) for 50 min
  5. filtrationThe mixture was filtered through Celite®
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resulting residue was partitioned with saturated NaHCO3 (100 mL) and CH2Cl2 (200 mL)
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated ill vacuo
  11. customto give the crude product

出典と根拠

ORDレコード
ord-55fe62d903f04c48888498c14a7e6246
出典データセット
uspto-grants-2006_03
特許番号
US07012074B2

反応ノート

読み込み中…