Benzyl Bromide → 2-(1-Benzylpiperidin-4-yloxy)-6-bromobenzo[d]thiazole

HRID 1429533Notes

Reaction equation

HRID 1429533 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([O:9][CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[S:8][C:4]=2[CH:3]=1.CCN(CC)CC.Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH2:26]([N:13]1[CH2:12][CH2:11][CH:10]([O:9][C:7]2[S:8][C:4]3[CH:3]=[C:2]([Br:1])[CH:17]=[CH:16][C:5]=3[N:6]=2)[CH2:15][CH2:14]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 674668246-Bromo-2-(piperidin-4-yloxy)-benzothiazole

Product 1

HCID 674675792-(1-Benzylpiperidin-4-yloxy)-6-bromobenzo[d]thiazoleYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 1B (4.32 g, 13.79 mmol) in THF (100 mL) was added Et3N (3.84 mL, 27.6 mmol) followed by (bromomethyl)benzene (1.64 mL, 13.8 mmol). Upon completion of addition, the reaction mixture was stirred at rt overnight. After this time, the reaction mixture was quenched with saturated aqueous NH4Cl (50 mL), and then extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (40 mL) and dried (MgSO4). The solvent was removed and the resulting residue was recrystallized from MeOH to give Compound 14A as a white solid (2.12 g, 5.26 mmol, 38% yield). LC/MS (m/z)=404 (M+H)+.

Workup

  1. additionUpon completion of addition
  2. customAfter this time, the reaction mixture was quenched with saturated aqueous NH4Cl (50 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organic layers were washed with brine (40 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed
  7. customthe resulting residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-1a17b8ca462042afbe3bd11e77d235fe
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

Loading…