1,2-Dichloroethane → HCID 9931708, compound

HRID 1611558Notes

Reaction equation

HRID 1611558 reaction equation
Cl.Cl.[CH:3]1([CH2:16][N:17]([CH3:19])[CH3:18])[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][CH2:5][NH:4]1.[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH2:28][C:29](O)=[O:30].O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C(Cl)CCl>CN(C=O)C.O>[Cl:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[CH2:28][C:29]([N:4]1[CH2:5][CH2:6][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[NH:14][C:15]=2[CH:3]1[CH2:16][N:17]([CH3:19])[CH3:18])=[O:30]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 882092,4-Dichlorophenylacetic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 22256586HCID 22256586, compound

Product 1

HCID 9931708HCID 9931708, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(1,2,3,4-tetrahydrobeta-carbolinyl)methyl]dimethylamine dihydrochloride (0.85 g, 2.80 mmole) in dry DMF (20 mL) at RT was 2,4-dichlorophenylacetic acid (0.63 g, 3.08 mmole), 1-hydroxybenzotriazole hydrate (0.42 g, 3.08 mmole) and diisopropylethylamine (1.19 g, 9.24 mmole). After 10 min, EDC (0.59 g, 3.08 mmole) was added and the reaction was allowed to stir for 12 hr. The reaction contents were poured into H2O (100 mL) and extracted with EtOAc (2×100 mL). The combined organic phases were washed sequentially with H2O and brine. Drying the organic phase over Na2SO4 and concentration under reduced pressure gave a yellow oil. Purification on silica [(CHCl3/CH3OH, 95:5 (containing 5% NH4OH)] afforded the title compound (1.05 g, 90%) as a yellow solid: MS (ES) m/e 417 (M+H)+.

Workup

  1. customat RT
  2. customThe reaction contents
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe combined organic phases were washed sequentially with H2O and brine
  5. customDrying the organic phase
  6. concentrationover Na2SO4 and concentration under reduced pressure
  7. customgave a yellow oil
  8. customPurification on silica [(
  9. additionCHCl3/CH3OH, 95:5 (containing 5% NH4OH)]

Sources & evidence

ORD record
ord-c1f70267c554454e8ec29fcf975fef8f
Source dataset
uspto-grants-2006_01
Patent number
US06987115B2

Reaction notes

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