Acetic Acid → HCID 66710911, compound

HRID 1261961Notes

Reaction equation

HRID 1261961 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25]([O:32][CH3:33])[CH:24]=3)[CH2:18]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(O)(=O)C.CCOC(C)=O.[BrH:44]>>[BrH:44].[CH3:33][O:32][C:25]1[CH:24]=[C:23]([N:19]2[CH2:20][CH2:21][CH2:22][CH:17]([N:14]3[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]3)[CH2:18]2)[CH:28]=[CH:27][C:26]=1[N+:29]([O-:31])=[O:30]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 66711201HCID 66711201, compound

Product 1

HCID 66710911HCID 66710911, compound

Procedure

A solution of 4-[1-(3-methoxy-4-nitro-phenyl)-piperidin-3-yl]-piperazine-1-carboxylic acid benzyl ester (300 mg, 0.66 mmol) in 4 M of hydrogen bromide in acetic acid (6 mL, 20 mmol) was heated at 40-45° C. for 45 min, then allowed to cool to room temperature while being stirred overnight. The orange homogenous solution was added dropwise to a vigorously stirred flask of EtOAc (50 mL) and the resulting precipitate was filtered, washed with EtOAc and dried in-vacuo to give 294 mg of an orange solid, used without further purification. MS=322 (M-HBr+1).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with EtOAc
  3. customdried in-vacuo

Sources & evidence

ORD record
ord-492035e5ab63406993dcfd6bc9b068af
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…