Diisopropylethylamine → HCID 66906271, compound

HRID 2040959Notes

Reaction equation

HRID 2040959 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7](Cl)[S:8][C:4]=2[CH:3]=1.Cl.[NH:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([OH:19])[CH2:14]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([N:13]3[CH2:18][CH2:17][CH2:16][C@H:15]([OH:19])[CH2:14]3)[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20498716-Bromo-2-chlorobenzothiazoleHCID 16211918(3S)-Piperidin-3-ol--hydrogen chloride (1/1)

Product 1

HCID 66906271HCID 66906271, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-bromo-2-chlorobenzo[d]thiazole (1.0 g, 4.0 mmol) and (S)-piperidin-3-ol hydrochloride (0.609 g, 4.43 mmol), and N,N-diisopropylethylamine (3.51 mL, 0.02012 mole) in N,N-dimethylformamide (2.0 mL) was heated to 150° C. under microwave irradiation for 15 minutes. The reaction mixture was transferred to a 100 mL round bottom flask (methanol rinse) and volatiles were removed under reduced pressure. The residue was partitioned between CHCl3 and saturated aqueous sodium carbonate. The organic layer was dried over MgSO4. Drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The crude material was purified by column chromatography on an Analogix IntelliFlash-280 (Analogix SF15-12 g, 100% CHCl3 to 60:40 CHCl3/ethyl acetate). Fractions containing product were combined and concentrated under reduced pressure to provide (S)-1-(6-bromobenzo[d]thiazol-2-yl)piperidin-3-ol.

Workup

  1. customThe reaction mixture was transferred to a 100 mL round bottom flask
  2. wash(methanol rinse) and volatiles
  3. customwere removed under reduced pressure
  4. customThe residue was partitioned between CHCl3 and saturated aqueous sodium carbonate
  5. dry with materialThe organic layer was dried over MgSO4
  6. customDrying agent
  7. customwas removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe crude material was purified by column chromatography on an Analogix IntelliFlash-280 (Analogix SF15-12 g, 100% CHCl3 to 60:40 CHCl3/ethyl acetate)
  10. additionFractions containing product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b11c62f504ad446db12a33a16ab244c4
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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