Hydrochloric Acid → HCID 53643946, compound

HRID 2379450Notes

Reaction equation

HRID 2379450 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([OH:15])[C:12]=1[O:13][CH3:14])[CH:9]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[NH:8][CH2:7][CH2:6]2.Cl.C1C=CC2N([OH:35])N=NC=2C=1.[CH2:36]([N:38]([CH2:41]C)[CH2:39]C)[CH3:37].CCN=C=NCCCN(C)C>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([OH:15])[C:12]=1[O:13][CH3:14])[CH:9]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)[N:8]([C:37](=[O:35])[CH2:36][N:38]([CH3:41])[CH3:39])[CH2:7][CH2:6]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 9818855HCID 9818855, compound

Product 1

HCID 53643946HCID 53643946, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 6,7-dimethoxy-1-(4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-8-ol (103 mg, 0.312 mmole) in dichloromethane (2 ml) were added N,N-dimethylglysine hydrochloride (52.2 mg, 0.374 mole) and HOBt (57.3 mg, 0.374 mmole) at room temperature under nitrogen. Then triethylamine (56.5 μl, 0.405 mmole) and EDCI (71.7 mg, 0.374 mmole) were added to the mixture at 0° C. The reaction mixture was stirred at 0° C. for 1.5 hours and at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with chloroform. The combined extracts were successively washed with a saturated aqueous sodium hydrogencarbonate solution and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from methanol to give the desired compound (78.4 mg) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. washThe combined extracts were successively washed with a saturated aqueous sodium hydrogencarbonate solution and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-0fdbb02e165d4ae78f99e79dcdf067af
Source dataset
uspto-grants-1994_11
Patent number
US05362736

Reaction notes

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