Hydrochloric Acid → 1-[(Tert-butyl)oxycarbonyl]-3-(4-chlorobenzyl)piperidine-3-carboxylic acid

HRID 53235Notes

Reaction equation

HRID 53235 reaction equation
C([O:3][C:4]([C:6]1([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>C(O)(C)C>[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C:6]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)([C:4]([OH:5])=[O:3])[CH2:7]1)([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19962177Ethyl-3-(4-chlorobenzyl)-N-Boc-piperidin-3-caroxylate

Product 1

HCID 44644061-[(Tert-butyl)oxycarbonyl]-3-(4-chlorobenzyl)piperidine-3-carboxylic acidYield 83.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of Ethyl-3-(4-chlorobenzyl)-N-Boc-piperidin-3-caroxylate (36.4 g, 0.105 mol) in isopropyl alcohol (300 mL) was treated with 10N NaOH (300 mL). The mixture was heated at reflux for 48 hours. The reaction was cooled to room temperature and carefully neutralized by pouting over 1 L of crashed ice and adding 6 N HCl until pH 3. The mixture was then extracted with ethyl acetate (3×500 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated at reduced pressure to give 31 g of the product. 1H NMR CDCl3 δ 10.18 (br s), 7.26 (d, J=8.5 Hz, 2H), 7.04 (d, J=8.5 Hz, 2H), 3.95 (m, 1H), 3.6 (m, 1H), 3.2 (m, 2H), 2.90 (d, J=12 Hz, 1H), 2.78 (d, J=12 Hz, 1H), 2.00 (m, 1H), 1.75-1.30 (m, 3H), 1.44 (s, 9H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 48 hours
  3. extractionThe mixture was then extracted with ethyl acetate (3×500 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-858cf374a5e74476a7a0bd4f69fab133
Source dataset
uspto-grants-1997_04
Patent number
US05618830

Reaction notes

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