Morpholine → 4-((4-Bromothiazol-2-yl)methyl)morpholine

HRID 562283Notes

Reaction equation

HRID 562283 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC(O)=O>[Br:1][C:2]1[N:3]=[C:4]([CH2:7][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:5][CH:6]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 27631874-Bromothiazole-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 667233384-((4-Bromothiazol-2-yl)methyl)morpholineYield 76%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-1,3-thiazole-2-carbaldehyde (192 mg, 1.0 mmol) in DCM (4.0 mL) was added morpholine (130 ul, 1.5 mmol) and 3 drops of AcOH. The mixture was stirred for 12 hr and then Na(OAc)3BH (0.335 g, 1.5 mmol) was added. After 6 hr. the mixture was quenched with Sat. NaHCO3 (4.0 mL) and brine (3.0 mL). The organic layer was separated and concentrated to give 200 mg of 4-[(4-bromo-1,3-thiazol-2-yl)methyl]morpholine (76%).

Workup

  1. waitAfter 6 hr
  2. customthe mixture was quenched with Sat. NaHCO3 (4.0 mL) and brine (3.0 mL)
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-13a9c272d5e9426b9d3ef3704f449d34
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

Loading…