Benzaldehyde → 2-Benzylaminomethyl-1,2,3,4-tetrahydronaphthalene

HRID 1613657Notes

Reaction equation

HRID 1613657 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH3-]C#N.[Na+].Cl>CO>[CH2:13]([NH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 157186321,2,3,4-Tetrahydronaphthalen-2-ylmethanamine

Product 1

HCID 197742682-Benzylaminomethyl-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-aminomethyl-1,2,3,4-tetrahydronaphthalene (XXXI) (14.5 g), benzaldehyde (9.7 g) and NaBH3CN (5.8 g) in methanol (150 ml) was cooled to 0°. Concentrated HCl was added dropwise until the apparent pH (litmus) was 3-4. The mixture was then stirred 16 hours at 0°. The solvent was evaporated, and the residue was dissolved in EtOAc, which was washed with saturated NaHCO3 solution, dried (MgSO4), and evaporated. The residual oil was dissolved in MeOH, and a slight excess of concentrated HCl was added. Adding EtOAc and boiling caused precipitation of Compound XXXIV.HCl, which was collected by filtration. Its NMR was consistent with the structure indicated, and it was used without further purification.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwhich was washed with saturated NaHCO3 solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionThe residual oil was dissolved in MeOH
  7. additiona slight excess of concentrated HCl was added
  8. customprecipitation of Compound XXXIV
  9. filtrationHCl, which was collected by filtration
  10. customit was used without further purification

Sources & evidence

ORD record
ord-e7802faec47a4369aa556e84058164ff
Source dataset
uspto-grants-1993_03
Patent number
US05194450

Reaction notes

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