Benzylamine → N-Benzyl-1-amino-7-(pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalene

HRID 1611Notes

Reaction equation

HRID 1611 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH2:15][C:16]3=O)=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1C=CC=CC=1>[CH2:20]([NH:27][CH:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([O:8][CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH:18]=2)[CH2:13][CH2:14][CH2:15]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 189732117-(Pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 19691554N-Benzyl-1-amino-7-(pyridin-4-ylmethoxy)-1,2,3,4-tetrahydronaphthaleneYield 97.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of Compound 1 (820 mg, 3.24 mmol) and benzyl amine (354 μL, 3.24 mmol) in benzene (10 mL) was heated to reflux under azeotropic conditions. After the calculated amount of water was collected, the reaction was cooled and concentrated in vacuo. The residue was taken-up into ethanol (5 mL) and added to a slurry of sodium boroydride (246 mg, 6.48 mmol) in ethanol (15 mL). The reaction was heated to 80° C., stirred for 30 min, cooled and concentrated in vacuo. The residue was diluted with ethyl acetate followed by the slow addition of 1N hydrochloric acid. The layers were separated. The aqueous phase was adjusted to pH 7 with 2N sodium hydroxide and extracted with methylene chloride (2×). The organics were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel (elution with 5% methanol:methylene chloride) provided 1.09 g of Compound 12 as an oil.

Workup

  1. temperatureto reflux under azeotropic conditions
  2. customAfter the calculated amount of water was collected
  3. temperaturethe reaction was cooled
  4. concentrationconcentrated in vacuo
  5. additionadded to a slurry of sodium boroydride (246 mg, 6.48 mmol) in ethanol (15 mL)
  6. temperaturecooled
  7. concentrationconcentrated in vacuo
  8. additionThe residue was diluted with ethyl acetate
  9. additionfollowed by the slow addition of 1N hydrochloric acid
  10. customThe layers were separated
  11. extractionextracted with methylene chloride (2×)
  12. washwashed with brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e88b3e62b23f461dad90710584c27c0b
Source dataset
uspto-grants-1998_03
Patent number
US05726184

Reaction notes

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