Hydrochloric Acid → 2,3-dihydro-1H-inden-1-ylmethanamine

HRID 414176Notes

Reaction equation

HRID 414176 reaction equation
B#B.[CH:3]1([C:12]([NH2:14])=O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.Cl>C1COCC1>[CH:3]1([CH2:12][NH2:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1180992,3-dihydro-1H-indene-1-carboxamideHCID 6328200Diboron

Product 1

HCID 143486922,3-dihydro-1H-inden-1-ylmethanamineYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 150 ml of diborane (1M in THF) in 250 ml of dry THF. Ten g of 1-indane carboxamide is slowly added. Reaction mixture is stirred at reflux for three hours, cooled to room temperature, and worked up by slowly adding 150 ml of 1N HCl. THF is distilled off under reduced pressure, the aqueous solution is brought to pH~13 by addition of NaOH. It is extracted with ethyl acetate (2×300 ml). The organic extract is washed with water (1×100 ml), dried over MgSO4, filtered, and evaporated to dryness affording 6.5 g (71%) of 1-indanylmethylamine. It was used as is in the next reaction.

Workup

  1. customReaction mixture
  2. temperatureat reflux for three hours
  3. distillationTHF is distilled off under reduced pressure
  4. additionthe aqueous solution is brought to pH~13 by addition of NaOH
  5. extractionIt is extracted with ethyl acetate (2×300 ml)
  6. extractionThe organic extract
  7. washis washed with water (1×100 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-fffbbb39f9e8456e96f6c75472942f70
Source dataset
uspto-grants-1988_12
Patent number
US04791103

Reaction notes

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