Triethylamine → HCID 42629724, compound

HRID 1880614Notes

Reaction equation

HRID 1880614 reaction equation
[C:1](Cl)(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br.[Cl:13][C:14]1[C:23]([OH:24])=[C:22]([OH:25])[C:21]([Cl:26])=[C:20]2[C:15]=1[CH2:16][CH2:17][NH:18][CH2:19]2.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Cl:13][C:14]1[C:23]([OH:24])=[C:22]([OH:25])[C:21]([Cl:26])=[C:20]2[C:15]=1[CH2:16][CH2:17][N:18]([C:1](=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:19]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5354261Cinnamoyl ChlorideHCID 685081725,8-Dichloro-1,2,3,4-tetrahydroisoquinoline-6,7-diol--hydrogen bromide (1/1)

Product 1

HCID 42629724HCID 42629724, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

trans-Cinnamoyl chloride (79 mg, 0.476 mmol) was suspended in DMF (7 mL) together with 5,8-dichloro-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide (150 mg, 0.476 mmol) followed by triethylamine (133 μL, 0.952 mmol). The resulting mixture was stirred at room temperature for 16 hours and then diluted with ethyl acetate (50 mL). The resulting mixture was washed twice with saturated sodium bicarbonate (2×40 mL), dried (MgSO4) and evaporated into a yellowish mass. Purification with column chromatography (petroleum ether/ethyl acetate 1/1→1/2) yielded 69 mg (40%) of the title compound as a yellowish solid.

Workup

  1. washThe resulting mixture was washed twice with saturated sodium bicarbonate (2×40 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated into a yellowish mass
  4. customPurification with column chromatography (petroleum ether/ethyl acetate 1/1→1/2)

Sources & evidence

ORD record
ord-6983f06822ae459097d615c79b902fdb
Source dataset
uspto-grants-2012_11
Patent number
US08318768B2

Reaction notes

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