Hydrochloric Acid → 4-[3-(4-Bromophenyl)propyl]morpholine

HRID 270019Notes

Reaction equation

HRID 270019 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=O)=[CH:4][CH:3]=1.CSC.C(OCC)C.Cl>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 3283Diethyl EtherHCID 221798563-(4-Bromophenyl)-1-morpholinopropan-1-one

Product 1

HCID 221798324-[3-(4-Bromophenyl)propyl]morpholineYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 4B (760 mg, 2.550 mmol) in THF (10 mL) at room temperature was treated with 5M BH3/dimethylsulfide in diethyl ether (2.55 mL, 12.752 mmol), stirred for 24 hours, treated with 3N aqueous HCl (10 mL), heated to reflux for 1 hour, and partitioned between ethyl acetate and 1N NaOH. The aqueous layer was extracted with ethyl acetate (3×50 mL) and the combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% 2N NH3 in methanol/dichloromethane to provide the desired product (565 mg, 78%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. custompartitioned between ethyl acetate and 1N NaOH
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  5. dry with materialthe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with 5% 2N NH3 in methanol/dichloromethane

Sources & evidence

ORD record
ord-5d5db387f31447b5935b4035f1692332
Source dataset
uspto-grants-2008_11
Patent number
US07449485B2

Reaction notes

Loading…