Hydrochloric Acid → 4-(4-Bromo-benzyl)-2-phenyl morpholine

HRID 737068Notes

Reaction equation

HRID 737068 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.Cl.[C:11]1([CH:17]2[O:22][CH2:21][CH2:20][NH:19][CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:19]2[CH2:20][CH2:21][O:22][CH:17]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:18]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 707414-BromobenzaldehydeHCID 911012-Phenylmorpholine

Product 1

HCID 578495044-(4-Bromo-benzyl)-2-phenyl morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

429 mg of 4-Bromobenzaldehyde was dissolved in 6 mL of THF and 386 mg of the HCl salt of 2-Phenylmorpholine (Array) and 1.15 g of MP-BH(OAc)3 (2.77 mmol/g) was added. The reaction was agitated on an orbital shaker overnight at room temperature. The reaction was filtered and the resin washed several times with dichloromethane. The filtrate was concentrated and purified by flash chromatography. Yield: 281 mg.

Workup

  1. filtrationThe reaction was filtered
  2. washthe resin washed several times with dichloromethane
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-715723e31ae746169d3cfd6a7a320f4e
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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