Water → HCID 13132279, compound

HRID 1762302Notes

Reaction equation

HRID 1762302 reaction equation
[ClH:1].[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.O.[OH-].[NH4+].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C(#N)C>[ClH:1].[CH2:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:11][CH:3]1[NH:2][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 79177tert-Butyl bromoacetateHCID 1227642-Aminoindan hydrochloride

Product 1

HCID 13132279HCID 13132279, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Acetonitrile (800 ml) is added to 2-aminoindan hydrochloride (50 g, 0.295 mole) followed by the addition of water (100 ml) and concentrated ammonium hydroxide (100 ml). To the resulting stirring solution tert-butyl bromoacetate (60 g, 0.308 mole) in acetonitrile (150 ml is added dropwise at room temperature and the resulting mixture stirred overnight at room temperature. The acetonitrile is evaporated on a rotary evaporator, water added to the residue and the product extracted several times into methylene chloride. The combined methylene chloride extract is washed twice with water, dried over magnesium sulfate, filtered and evaporated to afford the crude product as a tan oil. The crude product is purified further by silica-gel chromatography (chloroform). The desired fractions are concentrated and the hydrochloride prepared with ether-hydrochloric acid to afford tert-butyl N-(2,3-dihydro-1H-inden-2-yl)glycinate hydrochloride as a colorless solid (60 g, 72%); m.p. 175°; mass spectra (CI): 248(m+1, 100%).

Workup

  1. additionis added dropwise at room temperature
  2. customThe acetonitrile is evaporated on a rotary evaporator, water
  3. additionadded to the residue
  4. extractionthe product extracted several times into methylene chloride
  5. extractionThe combined methylene chloride extract
  6. washis washed twice with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto afford the crude product as a tan oil
  11. customThe crude product is purified further by silica-gel chromatography (chloroform)
  12. concentrationThe desired fractions are concentrated
  13. customthe hydrochloride prepared with ether-hydrochloric acid

Sources & evidence

ORD record
ord-e46d727878064d8a848e971def9ed17c
Source dataset
uspto-grants-1989_05
Patent number
US04831184

Reaction notes

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