Acetic Acid Mixture with Hydrobromic Acid → HCID 66977230, compound

HRID 712206Notes

Reaction equation

HRID 712206 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]#[N:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.Br.C(O)(=[O:25])C>>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:14]([NH2:15])=[O:25])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 66977267HCID 66977267, compound

Product 1

HCID 66977230HCID 66977230, compound

Procedure

A solution of 1-(5-bromopyrimidin-2-yl)-4-phenylpiperidine-4-carbonitrile (0.31 g, 0.9 mmol) in HBr-acetic acid (12 mL) was refluxed for 16 h. After completion of reaction (by TLC), the mixture was poured into 100 mL of ice cold water and extracted with EtOAc (3×150 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated to obtain the desired product as a white solid (0.12 g). MS: 361.15 [M+H]+.

Workup

  1. customAfter completion of reaction (by TLC)
  2. extractionextracted with EtOAc (3×150 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f7e110d17e4c4d5482ff3588367bae5d
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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