2-(3,4-Dichlorophenyl)-6-(phenylmethoxy)-1-{4-[(2-piperidyl)ethoxy]benzyl}-1,2,3,4-tetrahydroisoquinoline → 2-(3,4-Dichlorophenyl)-1-{4-[(2-Piperidyl)Ethoxy]Benzyl}-1,2,3,4-Tetrahydroisoquinolin-6-Ol

HRID 2114725ノート

反応式

HRID 2114725 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19]CC4C=CC=CC=4)[CH:15]=3)[CH:10]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][NH:38]3)=[CH:30][CH:29]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=3)[CH:10]2[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][NH:38]3)=[CH:30][CH:29]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

3

反応物 1

HCID 543911702-(3,4-Dichlorophenyl)-6-(phenylmethoxy)-1-{4-[(2-piperidyl)ethoxy]benzyl}-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 693128582-(3,4-Dichlorophenyl)-1-{4-[(2-Piperidyl)Ethoxy]Benzyl}-1,2,3,4-Tetrahydroisoquinolin-6-Ol収率 3.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-(3,4-dichlorophenyl)-6-(phenylmethoxy)-1-{4-[(2-piperidyl)ethoxy]benzyl}-1,2,3,4-tetrahydroisoquinoline (0.380 g, 0.63 mmol) was placed under a nitrogen atmosphere and dissolved in ethyl acetate (5 ml). The flask was evacuated and flushed with nitrogen. To the flask was added palladium (10% wt. on activated carbon, 0.190 g). The flask was flushed and evacuated with nitrogen followed by hydrogen. The reaction was allowed to stir under the hydrogen atmosphere at room temperature for 5 hours. The reaction mixture was filtered through celite and concentrated. The product was purified by preparative HLPC (C-18 column, 10-100% acetonitrile/water with 0.1% trifluoroacetic acid) to provide the title compound (0.010 g, 3% yield). 1H NMR (CDCl3) 6.7-7.2 (m, 10H), 4.7 (t, 1H), 4.2-4.4 (m, 2H), 3.6-4.0 (m, 4H), 3.3-3.6 (m, 3H), 3.0-3.1 (m, 1H), 2.7-2.9 (m, 3H), 2.6-2.7 (m, 1H), 1.8-2.1 (m, 4H), 1.4 (m, 2H); ES-MS (m/z) 511 [M+H]+.

後処理

  1. customThe flask was evacuated
  2. customflushed with nitrogen
  3. additionTo the flask was added palladium (10% wt. on activated carbon, 0.190 g)
  4. customThe flask was flushed
  5. customevacuated with nitrogen
  6. filtrationThe reaction mixture was filtered through celite
  7. concentrationconcentrated
  8. customThe product was purified by preparative HLPC (C-18 column, 10-100% acetonitrile/water with 0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-0d815a8d83554672b756b696d0e7d403
出典データセット
uspto-grants-2008_10
特許番号
US07435729B2

反応ノート

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