Diisopropylethylamine → 4-Piperidineacetic acid

HRID 1989865Notes

Reaction equation

HRID 1989865 reaction equation
NC1C=CC([N:8]2[CH2:13][CH2:12][CH:11]([CH:14](C3C=CC=CC=3)[C:15]([O:17]C)=[O:16])[CH2:10][CH2:9]2)=CC=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 22499374(+/-)-Methyl 1-(4-aminophenyl)-alpha-phenyl-4-piperidineacetate

Product 1

HCID 15125944-Piperidineacetic acidYield 399.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DMF (0.5 ml) was added to a solution of 2-biphenylcarboxylic acid (0.077 mol) in DCM (250 ml). Thionyl chloride (0.154 mol) was added. The mixture was stirred and refluxed for 1 hour. The solvent was evaporated and then co-evaporated twice with DCM (100 ml). The residue was dissolved in DCM (100 ml) to give solution (A). Intermediate (18) (0.077 mol) and DIPEA (0.154 mol) were stirred in DCM (400 ml). Solution (A) was added. The mixture was stirred at room temperature for 3 hours and then washed with water. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 44 g of 4-piperidineacetic acid, 1-[4-[([1,1′-biphenyl]-2-ylcarbonyl)amino]phenyl]-α-phenyl-, methyl ester (intermediate 21).

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ccaae5a0127347d085793df7ef5f7456
Source dataset
uspto-grants-2010_01
Patent number
US07642378B2

Reaction notes

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