Hydrochloric Acid → 1-(5-Bromopyridin-2-yl)-N,N-dimethylpyrrolidin-3-amine

HRID 1916587Notes

Reaction equation

HRID 1916587 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4]C=1.[CH3:9][N:10]([CH3:16])[CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1.C([N:19](C(C)C)C(C)C)C.Cl>C(O)CCC.CCOC(C)=O.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:13]2[CH2:14][CH2:15][CH:11]([N:10]([CH3:16])[CH3:9])[CH2:12]2)=[N:19][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 78041,4-DibromobenzeneHCID 81531DiisopropylethylamineHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

HCID 115942111-(5-Bromopyridin-2-yl)-N,N-dimethylpyrrolidin-3-amine

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 215 mg (0.88 mmol) 2,5-dibromobenzene, 100 mg (0.88 mmol) 3-(dimethylamino)-pyrrolidine and 0.60 mL (3.51 mmol) ethyldiisopropylamine in 0.5 mL n-butanol is stirred for 30 min in the microwave at 150° C. The solvent is eliminated i.vac. and the residue is taken up in 20 mL EtOAc and 10 mL water. The aqueous phase is acidified with 1 M HCl. The phases are separated and then the aqueous phase is made alkaline with 2 M Na2CO3 solution and extracted with 40 mL EtOAc. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac.

Workup

  1. customThe phases are separated
  2. extractionextracted with 40 mL EtOAc
  3. dry with materialThe organic phase is dried over Na2SO4

Sources & evidence

ORD record
ord-d386550446a548d58827372b30057a63
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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