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Phosphorus oxychloride → 6,7-Bis-benzyloxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 2238351
ノート
印刷プレビュー

反応式

HRID 2238351 の反応式
[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:15]([O:27][CH2:28]C3C=CC=CC=3)[CH:14]=2)=O)=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:43])=O.[BH4-].[Na+]>C(#N)C.Cl>[ClH:43].[CH2:28]([O:27][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][C:16]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:8]([CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:2][CH:3]=1)[NH:10][CH2:11][CH2:12]2)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 24813Phosphorus oxychlorideHCID 4311764Sodium borohydrideHCID 117858292-biphenyl-4-yl-N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-acetamide

生成物 1

HCID 160865076,7-Bis-benzyloxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydroisoquinoline hydrochloride

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒
HCID 6342
Acetonitrile
溶媒

実験手順

6,7-bis-benzyloxy-1-biphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline hydrochloride (2) was prepared as follows: A stirred solution of 3 g (5.69 mmol) of 2-biphenyl-4-yl-N-[2-(3,4-bis-benzyloxy-phenyl)-ethyl]-acetamide and 5.6 ml (60 mmol) of phosphorus oxychloride in 25 ml of anhydrous acetonitrile was refluxed for 20 hours. The reaction solution was evaporated under reduced pressure and the residue was dissolved in 25 ml of methanol. To this stirred solution at 0° C., 2.27 g (60 mmol) of sodium borohydride was added portionwise. The stirred reaction mixture was allowed to reach room temperature overnight and then it was poured in 150 ml of 10% aqueous HCl solution. The precipitate was collected on a glass filter funnel, washed with water (3×50 ml), and air-dried overnight. The solid was recrystallized using ether/methanol mixture to provide 2.56 g (82%) of off-white crystals, mp 187-189° C.

後処理

  1. customThe reaction solution was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in 25 ml of methanol
  3. customThe stirred reaction mixture
  4. customThe precipitate was collected on a glass
  5. filtrationfilter funnel
  6. washwashed with water (3×50 ml)
  7. customair-dried overnight
  8. customThe solid was recrystallized

出典と根拠

ORDレコード
ord-b88fa517a65d49f5b0aee3feb768cdd8
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07718672B2

反応ノート

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