Benzaldehyde → 3-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine

HRID 1025398Notes

Reaction equation

HRID 1025398 reaction equation
[N:1]1([CH2:8][CH2:9][CH2:10][NH2:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH-](OC(C)=O)(OC(C)=O)O[C:22](C)=O.[Na+].C=O.[OH-].[Na+]>C(Cl)Cl>[N:1]1([CH2:8][CH2:9][CH2:10][N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:22])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 27643953-(Azepan-1-yl)propan-1-amineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 585405163-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-(Azepan-1-yl)propan-1-amine (0.10 g, 0.64 mmole) in methylene chloride (5 mL) were added benzaldehyde (0.64 mmole) and NaBH(OAc)3 (0.63 g, 3.0 mmol). The reaction solution was stirred at room temperature for 3 h. Then, paraformaldehyde (200 mg) was added to the reaction mixture and stirring was continued for 6 h. 2N aqueous NaOH (2 mL) was added to quench the reaction, followed by addition of methylene chloride (30 mL). The organic layer was separated, dried over anhydrous Na2SO4, and filtered. The filtrate was evaporated to supply 3-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine (151 mg).

Workup

  1. stirringstirring
  2. waitwas continued for 6 h
  3. customto quench
  4. customthe reaction
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to supply 3-(azepan-1-yl)-N-benzyl-N-methylpropan-1-amine (151 mg)

Sources & evidence

ORD record
ord-f21b74ff1a3e4dc2a06628c956941480
Source dataset
uspto-grants-2014_05
Patent number
US08729081B2

Reaction notes

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