Hydrochloric Acid → Ethyl 1-(6-chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate Hydrochloride

HRID 1700363Notes

Reaction equation

HRID 1700363 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][NH:13][C:14]([C:16]1([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17]1)=O.O=P(Cl)(Cl)Cl.Cl>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:14]([C:16]3([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17]3)[NH:13][CH2:12][CH2:11][C:5]2=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 24813Phosphorus oxychlorideHCID 11163887Ethyl 1-({[2-(5-chloro-1H-indol-3-yl)ethyl]amino}carbonyl)cyclobutanecarboxylate

Product 1

HCID 18317933Ethyl 1-(6-chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate Hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

32 g of the product obtained in Step A are heated at reflux in a solution of 400 ml of toluene and 35 ml of POCl3. After 3 hours, the reaction mixture is concentrated under reduced pressure, the residue is taken up in 300 ml of ethanol, and 5 g of sodium borohydride are slowly added. After 30 minutes, 300 ml of water are added and the ethanol is distilled off. After extraction of the residue with dichloromethane, drying and evaporation under reduced pressure, the oily residue obtained is converted into the hydrochloride in an ethanolic hydrogen chloride solution. The expected product is isolated by filtration and drying in vacuo.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. addition5 g of sodium borohydride are slowly added
  3. waitAfter 30 minutes
  4. addition300 ml of water are added
  5. distillationthe ethanol is distilled off
  6. extractionAfter extraction of the residue with dichloromethane
  7. customdrying
  8. customevaporation under reduced pressure
  9. customthe oily residue obtained

Sources & evidence

ORD record
ord-616e491ac5bd455682e9b3fd5465aff7
Source dataset
uspto-grants-2002_02
Patent number
US06350757B1

Reaction notes

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