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Dichloromethane → 4-((3-Bromothiophen-2-yl)methyl)morpholine

HRID 2190255
Notes
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Reaction equation

HRID 2190255 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=O.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(Cl)Cl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCOC(C)=O>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 27970793-Bromothiophene-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 234378474-((3-Bromothiophen-2-yl)methyl)morpholineYield 84.4%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of 3-bromothiophene-2-carbaldehyde (500 mg, 2.62 mmol) and morpholine (0.68 mL, 7.85 mmol) and CH2Cl2 (10 mL) was added sodium triacetoxyborohydride (1.11 g, 5.24 mmol). The mixture was stirred at room temperature overnight. The resulting mixture was diluted with EtOAc (100 mL) and the organic layer was washed with brine then dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (silica, 0-5% MeOH in CH2Cl2) to afford the sub-title compound (580 mg, 84%).

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialthen dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica, 0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5381ad921d964fcfabc70626713bb363
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324264B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes