Acetic Acid → HCID 21914376, compound

HRID 716737Notes

Reaction equation

HRID 716737 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH3:10])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 7363321-(4-Bromophenyl)propan-2-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21914376HCID 21914376, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(4-Bromophenyl)propan-2-one (2.03 g) was dissolved in CHCl3 (40 mL), and morpholine (1.24 mL) was added thereto, followed by stirring at room temperature overnight and then at 60° C. for 4 hours. NaBH(OAc)3 (4.03 g) and acetic acid (1.1 mL) were sequentially added thereto, followed by stirring overnight. The reaction was terminated by addition of water, and the reaction solution was separated between CHCl3 and a saturated aqueous NaHCO3 solution. The residue was purified by silica gel column chromatography (mobile phase: CHCl3/EtOAc=80/20 to 60/40 (v/v)) to yield the title compound (1.67 g, colorless oil).

Workup

  1. waitat 60° C. for 4 hours
  2. stirringby stirring overnight
  3. customThe reaction was terminated by addition of water
  4. customthe reaction solution was separated between CHCl3
  5. customThe residue was purified by silica gel column chromatography (mobile phase: CHCl3/EtOAc=80/20 to 60/40 (v/v))

Sources & evidence

ORD record
ord-5e7e0c836596434da94647875aeddddf
Source dataset
uspto-grants-2015_11
Patent number
US09193695B2

Reaction notes

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