Hydrochloric Acid → 3,3-dimethyl-2,3-dihydro-1H-inden-1-amine

HRID 850018Notes

Reaction equation

HRID 850018 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:19].[Na+].Cl>CO>[NH2:19][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:12])([CH3:1])[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3046283,3-Dimethyl-1-indanoneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 230089363,3-dimethyl-2,3-dihydro-1H-inden-1-amineYield 40.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,3-Dimethyl-1-(N-methyl-N-methylsulfonyl)aminoindan ##STR18## a) A solution of 25.0 g (0.156 mol) of 3,3-dimethylindan-1-one (Chem. Ber. 64, 1931, 1493) in 700 ml of methanol was stirred with 120.2 g (1.56 mol) of ammonium acetate and 69.1 g (1.1 mol) of sodium cyanoborohydride at 60° C. for 8 h. The reaction mixture was adjusted to pH<2 using dilute hydrochloric acid and concentrated using a rotary evaporator. The residue was taken up in dilute hydrochloric acid and extracted with EA, and the aqueous phase was then made alkaline using potassium carbonate solution and extracted with EA. The organic phase was dried with magnesium sulfate and concentrated under reduced pressure, giving 10.3 g of 1-amino-3,3-dimethylindan.

Workup

  1. concentrationconcentrated
  2. customa rotary evaporator
  3. extractionextracted with EA
  4. extractionextracted with EA
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4396448b3fd34c0eaf382539ae113b9e
Source dataset
uspto-grants-2000_01
Patent number
US06015822

Reaction notes

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