Benzaldehyde → 1-Benzyl-hexahydro-4H-azepin-4-one

HRID 1364110Notes

Reaction equation

HRID 1364110 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].C(=O)C1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16](O[BH-](OC(=O)C)OC(=O)C)(=[O:18])[CH3:17].[Na+].[OH-].[Na+]>ClCCl>[C:2]1([CH2:1][N:3]2[CH2:6][CH2:7][CH2:17][C:16](=[O:18])[CH2:5][CH2:4]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15143501-Benzyl-hexahydro-4H-azepin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(may be prepared as described in Synthetic Communications (1992), 22(9), 1249-58) was suspended in dichloromethane (100 ml) and triethylamine (9.31 ml, 66.9 mmol) added, followed by benzaldehyde (68 ml, 0.669 mol). The mixture was stirred at room temperature for 30 minutes under argon, then cooled in ice whilst sodium triacetoxyborohydride (17 g, 80 mmol) was added portionwise. The mixture was stirred and allowed to reach room temperature, then stirred for 2 hours. 2M sodium hydroxide solution (80 ml) was added, the layers separated and the aqueous layer extracted with dichloromethane (×2). The combined organic extracts were evaporated to half volume, then extracted with 2M hydrochloric acid (2×100 ml). The aqueous layer was made basic with 50% sodium hydroxide solution and extracted with dichloromethane (×2). The combined organic extracts were dried over magnesium sulphate and evaporated to afford the title compound (D2). 1H NMR (CDCl3) δ 1.82-1.88 (2H, m), 2.52-2.55 (2H, m), 2.59-2.62 (2H, m) 2.71-2.76 (4H, m) 3.65 (1H, s) 7.23-7.33 (5H, m).

Workup

  1. custom(may be prepared as described in Synthetic Communications (1992), 22(9), 1249-58)
  2. additionwas added portionwise
  3. stirringThe mixture was stirred
  4. customto reach room temperature
  5. stirringstirred for 2 hours
  6. customthe layers separated
  7. extractionthe aqueous layer extracted with dichloromethane (×2)
  8. customThe combined organic extracts were evaporated to half volume
  9. extractionextracted with 2M hydrochloric acid (2×100 ml)
  10. extractionextracted with dichloromethane (×2)
  11. dry with materialThe combined organic extracts were dried over magnesium sulphate
  12. customevaporated

Sources & evidence

ORD record
ord-0e10aaebea7e49c69a9e0a715934c281
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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