Triethylamine → HCID 67047003, compound

HRID 1670825Notes

Reaction equation

HRID 1670825 reaction equation
Cl.[F:2][C:3]1([F:9])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.N(CC)(CC)CC.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:22][O:21][C:19](=[O:20])[CH2:18][N:6]1[CH2:7][CH2:8][C:3]([F:9])([F:2])[CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 516892Sodium BicarbonateHCID 27583514,4-Difluoropiperidine hydrochloride

Product 1

HCID 67047003HCID 67047003, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Treat a ° C. solution of 4,4-difluoropiperidin HCl (17.91 g, 0.113 mol) and (CH3CH2)3N (28.75 g, 0.284 mol) in CH2Cl2 (250 mL) with methyl bromoacetate (17.37 g, 0.113 mol), warm to room temperature, and stir 16 hours at room temperature under N2. Dilute the reaction with saturated NaHCO3 and water and extract twice with 3:1 chloroform:isopropanol. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with 0 to 5% methanol in CH2Cl2 to afford 14.22 g (65%) of the titled product. Rf=0.77 (9/1 CH2Cl2/methanol). ES MS (m/z): 194 (M+).

Workup

  1. additionTreat a ° C
  2. additionDilute
  3. extractionextract twice with 3:1 chloroform
  4. dry with materialDry the organic layer (Na2SO4)
  5. customremove the solvent in vacuo
  6. customto afford crude product
  7. custompurify with 0 to 5% methanol in CH2Cl2

Sources & evidence

ORD record
ord-48c90600c2cc48e29c453567a090a3db
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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