Ethanolamine → 1-[3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinoline-4-yl)-phenyl]-3-(2-hydroxy-ethyl)-urea

HRID 1072529Notes

Reaction equation

HRID 1072529 reaction equation
Cl.[N+](C1C=CC([O:11][C:12](=O)[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]3[C:29]4[C:24](=[C:25]([Cl:31])[CH:26]=[C:27]([Cl:30])[CH:28]=4)[CH2:23][N:22]([CH3:32])[CH2:21]3)[CH:15]=2)=CC=1)([O-])=O.[NH2:34][CH2:35][CH2:36][OH:37]>CN(C=O)C>[Cl:30][C:27]1[CH:28]=[C:29]2[C:24](=[C:25]([Cl:31])[CH:26]=1)[CH2:23][N:22]([CH3:32])[CH2:21][CH:20]2[C:16]1[CH:15]=[C:14]([NH:13][C:12]([NH:34][CH2:35][CH2:36][OH:37])=[O:11])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 223868924-Nitrophenyl [3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]carbamate hydrochloride2×

Product 1

HCID 223868231-[3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinoline-4-yl)-phenyl]-3-(2-hydroxy-ethyl)-ureaYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

509 mg (1,0 mmol) [3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenyl]-carbamic-acid 4-nitro-phenyl-ester-Hydrochloride (example 151, intermediate 1) were dissolved in 15 ml DMF and at 0° C. a solution of 67,2 mg (1,1 mmol) of 2-Aminoethanol in 10 ml DMF was added. After stirring for 3 h at room temperature the solvent was removed i. vac. The residue was dissolved in ethylacetate and washed with sat. NaHCO3-solution. The organic layer was separated and the aqueous layer was extracted twice with ethylacetate. The combined organic layers were washed with sat. NaCl-solution, dried (MgSO4) and concentrated. Purification by silica gel chromatography (dichloromethane/methanol) yielded 265 mg of the title compound.

Workup

  1. additionwas added
  2. customwas removed i
  3. dissolutionThe residue was dissolved in ethylacetate
  4. washwashed with sat. NaHCO3-solution
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted twice with ethylacetate
  7. washThe combined organic layers were washed with sat. NaCl-solution
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customPurification by silica gel chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-57880f55dc6d4b259b281e3a73f6a729
Source dataset
uspto-grants-2005_06
Patent number
US06911453B2

Reaction notes

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