Hydrogen Bromide → HCID 86639591, compound

HRID 1910832Notes

Reaction equation

HRID 1910832 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.S(Cl)(Cl)=O.[CH3:15][Si](C=[N+]=[N-])(C)C.[BrH:22]>ClCCl.C(O)(=O)C>[BrH:22].[Br:22][CH2:15][C:8]([CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)=[O:10]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 24386Thionyl ChlorideHCID 167693TrimethylsilyldiazomethaneHCID 27369391-Methylpiperidine-4-carboxylic acid

Product 1

HCID 86639591HCID 86639591, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-methyl-piperidine-4-carboxylic acid (0.40 g, 2.79 mmol) and thionyl chloride (0.32 mL, 4.44 mmol) in dichloromethane (10 mL) was heated to reflux for 6 h. The reaction mixture was distilled under reduced pressure and the residue dissolved in dry acetonitrile (4 mL). Trimethylsilyl diazomethane (4 mL, 8.08 mmol) was added and the mixture stirred for 2 h at ambient temperature. The reaction was cooled to 0° C. and 30% HBr in acetic acid (2 mL) added dropwise. The reaction mixture was warmed to room temperature and stirred for 1 h. The precipitate was filtered and washed with ether to afford 2-bromo-1-(1-methyl-piperidin-4-yl)-ethanone hydrobromide (200 mg, 33%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. distillationThe reaction mixture was distilled under reduced pressure
  4. dissolutionthe residue dissolved in dry acetonitrile (4 mL)
  5. temperatureThe reaction was cooled to 0° C.
  6. temperatureThe reaction mixture was warmed to room temperature
  7. stirringstirred for 1 h
  8. filtrationThe precipitate was filtered
  9. washwashed with ether

Sources & evidence

ORD record
ord-7b4147622449438190f4645805481f28
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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