Dimethylamine → 4-(4-Bromo-1-(2-(dimethylamino)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1685168Notes

Reaction equation

HRID 1685168 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:20][CH2:21]OS(C)(=O)=O)[CH:16]=[C:17]([Br:19])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][NH:28][CH3:29]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:20][CH2:21][N:28]([CH3:29])[CH3:27])[CH:16]=[C:17]([Br:19])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86641601tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 672650004-(4-Bromo-1-(2-(dimethylamino)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylic acid tert-butyl esterYield 83.33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Add 4-[4-bromo-1-(2-methanesulfonyloxy-ethyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (10.2 g; 0.023 mol; 1.0 equiv), dimethyl amine (40% aqueous solution, 22 mL; 0.18 mol; 8.0 equiv) in ACN (100 mL) and stir at 100° C. for 3 h. Concentrate, quench the reaction with saturated NaHCO3 solution and extract with EA. Concentrate the organic layer; purify over a silica gel column with EA/hexane to give the title compound (7.5 g; 83.33%).

Workup

  1. concentrationConcentrate
  2. customquench
  3. customthe reaction with saturated NaHCO3 solution
  4. extractionextract with EA
  5. concentrationConcentrate the organic layer
  6. custompurify over a silica gel column with EA/hexane

Sources & evidence

ORD record
ord-2bcd4f123871435986cd76327d5313c7
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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