Morpholine → 4-[(5-Bromothiophen-2-yl)methyl]morpholine

HRID 2421340Notes

Reaction equation

HRID 2421340 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1(C=O)[CH2:12][CH:11]=C[S:9]1.C(O[BH-](O[C:25](=O)[CH3:26])OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:7][C:8]1[S:9][C:25]([CH2:26][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 866100842-Bromothiophene carboxaldehyde

Product 1

HCID 219142724-[(5-Bromothiophen-2-yl)methyl]morpholineYield 148.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Morpholine (0.96 g) was added portionwise to a solution of 2-bromothiophene carboxaldehyde (1.195 g) in tetrahydrofuran (50 ml). After stirring at room temperature for 5 minutes, sodium triacetoxyborohydride (3.18 g) was added and the mixture stirred at room temperature for a further 3 h. The mixture was added to saturated aqueous sodium bicarbonate (100 ml) and extracted twice with ethyl acetate. The combined extracts were evapourated to dryness. The product was purified by column chromatography elutinig with ethyl acetate in hexane mixtures to give a yellow oil (2.414 g).

Workup

  1. stirringthe mixture stirred at room temperature for a further 3 h
  2. extractionextracted twice with ethyl acetate
  3. customThe product was purified by column chromatography elutinig with ethyl acetate in hexane mixtures

Sources & evidence

ORD record
ord-91b4b598c0d143028677f86a1adab658
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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