1,2,3,4-Tetrahydroisoquinoline → HCID 21830900, compound

HRID 1600801Notes

Reaction equation

HRID 1600801 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][NH:16][CH2:15]1.O(CC)CC.[ClH:29]>C(#N)C.CCOCC>[ClH:29].[CH:17]1([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:15][NH:16]1

Participants

7

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10953452Ether hydrochloride

Product 1

HCID 21830900HCID 21830900, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

A solution of ethyl bromoacetate (20.9 g) in acetonitrile (30 mL) was added to a mixture of K2CO3 (27.6 g, 0.2 mol) and 1,2,3,4-tetrahydro-2-isoquinoline (13.3 g, 0.1 mol) in acetonitrile (220 mL). The reaction mixture was stirred at room temperature for about 2 days, and then was refluxed for 4 hours. The reaction mixture was filtered, the filtrate was concentrated in vacuo and the residue was partitoned between ether and water. The ether layer was separated, dried over MgSO4 and concentrated in vacuo to afford a liquid which was dissolved in ether (200 mL), cooled and treated with Et2O·HCl to afford 12,5 g (77%) of ethyl 1,2,3,4-tetrahydro-2-isoquinolinylacetate hydrochloride.

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe ether layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford a liquid which
  8. temperaturecooled

Sources & evidence

ORD record
ord-5ac21325edce4b8284cf5c130bbf1143
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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