Dimethylamine → HCID 67355408, compound

HRID 627358Notes

Reaction equation

HRID 627358 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]2[C:15](=O)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][NH:18][CH3:19]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:14][CH:13]2[CH:15]([N:18]([CH3:19])[CH3:17])[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 156391343-Benzyl-3-azabicyclo(3.2.1)octan-8-one

Product 1

HCID 67355408HCID 67355408, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-benzyl-3-azabicyclo[3.2.1]octan-8-one (107 mg, 0.50 mmol) in DCM (2 ml) was added dimethylamine (2 ml, 1M in THF) and the resulting reaction mixture was stirred at room temperature for 1H. Na(AcO)3BH (316 mg, 1.49 mmol) was added and the reaction mixture was stirred at room temperature overnight. When TLC shows completion reaction mixture was diluted with DCM and washed with water and brine. Combined aqueous layers were backextracted with DCM. Combined organic layers were dried over Na2SO4, filtered, concentrated and purified by column chromatography which gave 3-benzyl-N,N-dimethyl-3-azabicyclo[3.2.1]octan-8-amine (80 mg) in 67% yield. 1H NMR (400 MHz, MeOD) δ ppm 7.47-7.23 (m, 5H) 3.86 (s, 2H) 2.88 (d, J=11.62 Hz, 2H) 2.72 (dd, J=12.38, 3.28 Hz, 2H) 2.52 (s, 7H) 2.35 (br. s., 2H) 1.90-1.73 (m, 4H)

Workup

  1. customthe resulting reaction mixture
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. customcompletion reaction mixture
  4. washwashed with water and brine
  5. dry with materialCombined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography which

Sources & evidence

ORD record
ord-5e89546a0a664fa5836282eb4969ee70
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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