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 2304673Notes

Reaction equation

HRID 2304673 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-91a541c7c2664f019068c613a9533b90
Source dataset
uspto-grants-2002_08
Patent number
US06436923B1

Reaction notes

Loading…