Dichloromethane → HCID 67345002, compound

HRID 2036879Notes

Reaction equation

HRID 2036879 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.C(N(CC)CC)C.ClCCl.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>CN(C1C=CN=CC=1)C.O>[CH2:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 42614607Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride

Product 1

HCID 67345002HCID 67345002, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 10 g methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride, 10 ml triethylamine, and 15 ml dichloromethane with 525 mg DMAP is stirred at 0° C. and 9.3 ml of benzyl chloroformate are added dropwise. After stirring overnight at ambient temperature, the reaction mixture is added to cold water. The organic phase is washed, dried, and evaporated. The crude product is purified by a silica gel chromatography.

Workup

  1. stirringAfter stirring overnight at ambient temperature
  2. washThe organic phase is washed
  3. customdried
  4. customevaporated
  5. customThe crude product is purified by a silica gel chromatography

Sources & evidence

ORD record
ord-a6f8ec461b1c474186b1886233d3c357
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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