Hydrochloric Acid → HCID 4717165, compound

HRID 1529837Notes

Reaction equation

HRID 1529837 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[CH:11]1([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C([BH3-])#N.[Na+].Cl>C(#N)C.C(O)(=O)C>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH2:1][NH:17][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 115693-MethoxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 4717165HCID 4717165, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of m-anisaldeyde (500 mg, 3.67 mmol) and cyclohexylamine (420 μL, 3.67 mmol) in acetonitrile (30 mL) was stirred for 4 h and slowly treated with sodium cyanoborohydride (227 mg, 4.4 mmol). Glacial acetic acid was added until pH˜6 (pH paper), and the solution was stirred for 16 h. Conc. HCl (0.5 mL) was added and acetonitrile was evaporated under reduced pressure. The crude residue was quenched with water (100 mL) and extracted with ethyl acetate. The aqueous phase was basified with 10% aqueous NaOH until pH>7 and extracted with dichloromethane (3×50 mL). The organic phase was dried over magnesium sulfate, filtered, and evaporated under reduced pressure without heating to provide 670 mg of N-(3-methoxybenzyl)-cyclohexylamine (83% yield) as a light oil. 1H NMR (300 MHz, acetone-d6) δ 1.05-1.30 (m, 5H), 1.58 (m, 1H), 1.72 (m, 2H), 1.89 (m, 2H), 2.45 (m, 1H), 3.77 (s, 2H), 3.79 (s, 3H), 6.77 (dd, J=2.1 and 8.2 Hz, 1H), 6.92 (d, J=7.5 Hz, 1H), 6.96 (s, 1H), 7.21 (t, J=7.8 Hz, 1H) ppm.

Workup

  1. customacetonitrile was evaporated under reduced pressure
  2. customThe crude residue was quenched with water (100 mL)
  3. extractionextracted with ethyl acetate
  4. extractionextracted with dichloromethane (3×50 mL)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. temperaturewithout heating

Sources & evidence

ORD record
ord-ae0a238bce3342dcb271d92a8ed92f8e
Source dataset
uspto-grants-2015_07
Patent number
US09090651B2

Reaction notes

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