Water → (R)-5-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole

HRID 2040984Notes

Reaction equation

HRID 2040984 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:5]=2[N:6]=1.Cl.Cl.[NH:14]1[CH2:18][CH2:17][C@@H:16]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:11][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([N:14]3[CH2:18][CH2:17][C@@H:16]([N:19]4[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]4)[CH2:15]3)=[N:6][C:5]=2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 202512695-Bromo-2-chloro-1,3-benzothiazoleHCID 669057171-[(3R)-pyrrolidin-3-yl]piperidine dihydrochloride

Product 1

HCID 44124704(R)-5-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 2-chloro-5-bromobenzothiazole (CAS #824403-26-1, catalog #20284, Daxian Chemical Institute Ltd., #179, 10169 New Hampshire Ave., Silver Spring, Md. 20903, 2.485 g, 0.0100 mole), (R)-1-(pyrrolidin-3-yl)piperidine dihydrochloride (Reference Example 5c, 2.73 g, 0.0120 mole), and potassium carbonate (6.00 g, 0.04438 mole) in N,N-dimethylformamide (15 mL) is heated to 100° C. with an oil bath for 15 hours. The reaction mixture is cooled to room temperature then poured into water (300 mL). The resulting precipitate is collected by filtration and the filter cake is rinsed with water (600 mL). The solid is dissolved in dichloromethane and the solution is dried (MgSO4) and filtered. The filtrate is concentrated under reduced pressure to give a solid that is crystallized from hot ethyl acetate to give (R)-5-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationThe resulting precipitate is collected by filtration
  3. washthe filter cake is rinsed with water (600 mL)
  4. dissolutionThe solid is dissolved in dichloromethane
  5. dry with materialthe solution is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customto give a solid
  9. customthat is crystallized from hot ethyl acetate

Sources & evidence

ORD record
ord-c81c2307209d46f880c06bba31c8ca23
Source dataset
uspto-grants-2013_11
Patent number
US08580968B2

Reaction notes

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