N-benzyl-N-(5,6-dimethoxy-1-indanyl)glycine hydrochloride → N-(5,6-dimethoxy-1-indanyl)glycine

HRID 1248049Notes

Reaction equation

HRID 1248049 reaction equation
Cl.C([N:9]([CH:14]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=2)[CH2:16][CH2:15]1)[CH2:10][C:11]([OH:13])=[O:12])C1C=CC=CC=1>C(O)C.[C].[Pd]>[CH3:26][O:25][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][C:20]=1[O:23][CH3:24])[CH:14]([NH:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:15][CH2:16]2

Participants

4

Reactant 1

HCID 20280785N-benzyl-N-(5,6-dimethoxy-1-indanyl)glycine hydrochloride

Product 1

HCID 13472326N-(5,6-dimethoxy-1-indanyl)glycineYield 85.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

N-Benzyl-N-(5,6-dimethoxy-1-indanyl)glycine hydrochloride (14 g) is dissolved in 300 ml of ethanol, 3.0 g of 5% palladium-carbon is added and catalytic reduction is carried out at ordinary temperature and pressure. After absorption of the calculated amount of hydrogen, the catalyst is filtered off, and the ethanol is distilled off under reduced pressure. The residue is dissolved in 10 ml of water and adjusted to pH 7.0 with aqueous ammonia. The crystalline precipitates are collected by filtration, washed with a small amount of water, and dried, to give 8.0 g of N-(5,6-dimethoxy-1-indanyl)glycine as colorless needles. Melting point: 213°-216° C.

Workup

  1. customAfter absorption of the calculated amount of hydrogen
  2. filtrationthe catalyst is filtered off
  3. distillationthe ethanol is distilled off under reduced pressure
  4. dissolutionThe residue is dissolved in 10 ml of water
  5. customThe crystalline precipitates
  6. filtrationare collected by filtration
  7. washwashed with a small amount of water
  8. customdried

Sources & evidence

ORD record
ord-7e1aaa7c2056474abb958520d9448f26
Source dataset
uspto-grants-1985_06
Patent number
US04521607

Reaction notes

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