2-Bromoethanol → HCID 22643310, compound

HRID 2414828Notes

Reaction equation

HRID 2414828 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:8][CH2:7][CH2:6]2.Br[CH2:24][CH2:25][OH:26].CCN(C(C)C)C(C)C>O1CCCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:8]([CH2:24][CH2:25][OH:26])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 347546,7-Dimethoxy-1-(2-phenylethyl)-1,2,3,4-tetrahydroisoquinolineHCID 81531Diisopropylethylamine

Product 1

HCID 22643310HCID 22643310, compound

Reagents, catalysts & solvents 1

HCID 8894TetrahydropyranSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 6,7-dimethoxy-1-phenethyl-1,2,3,4-tetrahydro-isoquinoline (example A21, 59.5 mg, 0.2 mmol) and 2-bromoethanol (28.3 μL, 0.4 mmol) in tetrahydropyran (3 mL) is treated with DIPEA (68 μL, 0.4 mmol), and the reaction mixture is heated at 90° C. in a sealed flask for 5 days. The reaction is mixture evaporated to dryness, and the residue is purified by preparative HPLC, to provide the title compound.

Workup

  1. customevaporated to dryness
  2. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-c826d3d60372416590e89b3281510d63
Source dataset
uspto-grants-2004_11
Patent number
US06815451B2

Reaction notes

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