Hydrochloric Acid → 4-Methyl-2,3-dihydro-1H-inden-1-amine

HRID 1877330Notes

Reaction equation

HRID 1877330 reaction equation
[N:1]([CH:4]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C1COCC1.O>[CH3:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[CH2:6][CH2:5][CH:4]2[NH2:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 59860533HCID 59860533, compound

Product 1

HCID 227428304-Methyl-2,3-dihydro-1H-inden-1-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g (5.8 mmol) 1-azido-4-methyl-indane is treated with 4.54 g (17.3 mmol) triphenylphosphine in 26 ml THF and 1.4 ml H2O at room temperature overnight. Completion of the reaction is achieved by heating up the mixture for additional 2.5 hours. The reaction mixture is then cooled to room temperature and diluted with water. The pH is adjusted to 2 by adding cold (ca 0° C.) aqueous HCl (1M). After extraction with EtOAc the aqueous layer is separated, basified with NaOH (2M) and extracted into EtOAc. The organic layer is then dried (MgSO4) and concentrated in vacuo to give 4-methyl-indan-1-yl-amine as a light yellow liquid.

Workup

  1. temperatureby heating up the mixture for additional 2.5 hours
  2. extractionAfter extraction with EtOAc the aqueous layer
  3. customis separated
  4. extractionextracted into EtOAc
  5. dry with materialThe organic layer is then dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-295af8762d054868a5327767fdc869bd
Source dataset
uspto-grants-2012_11
Patent number
US08309739B2

Reaction notes

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