Ethanolamine → 5-[N-(2-hydroxyethyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1637264Notes

Reaction equation

HRID 1637264 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:18](=O)[CH2:17][CH2:16][C:15]=2[C:14]=34)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:20][CH2:21][CH2:22][OH:23].CO.C([BH3-])#N.[Na+]>C(Cl)Cl>[OH:23][CH2:22][CH2:21][NH:20][CH:18]1[C:13]2[C:14]3[C:15](=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[NH:8][C:9]=3[CH:10]=[CH:11][CH:12]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 193483682-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

Product 1

HCID 193482865-[N-(2-hydroxyethyl)amino]-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indoleYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A portion (0.20 g) of the compound obtained in Example 41 and 2-aminoethanol (0.49 ml) were suspended in a mixed solvent of methanol (3 ml) and methylene chloride (2 ml) and to the suspension was added sodium cyanoborohydride (61 mg). The mixture was stirred for 13 hours at room temperature and heated to reflux for further 8 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, followed by extraction with three portions of methylene chloride. The organic layers were combined, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (methylene chloride/methanol=19:1) and further crystallized from ether to yield 75 mg (32%) of the titled compound as yellowish brown crystals.

Workup

  1. temperatureheated
  2. temperatureto reflux for further 8 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionfollowed by extraction with three portions of methylene chloride
  6. washwashed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=19:1)
  10. customfurther crystallized from ether

Sources & evidence

ORD record
ord-42b03a779ff046ad8a67abe15fdaa0c7
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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