Hydrochloric Acid → 910442-78-3

HRID 1479029Notes

Reaction equation

HRID 1479029 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([O:23]C)=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([OH:23])=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89650227HCID 89650227, compound

Product 1

HCID 45074026910442-78-3Yield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(2-methoxycarbonyl-benzyl)-piperidine-1-carboxylic acid tert-butyl ester (330 mg; 0.99 mmol; 1 eq.) and 1M NaOH (2 mL; 2 mmol; 2 eq.) in EtOH (3 mL) was stirred at 60° C. for 16 hours. The pH was made acidic with 1M HCl and the mixture extracted with DCM (2×). The combined organic phase was dried over magnesium sulfate and concentrated in vacuo to afford the title compound (295 mg, 93%) as a white solid. HPLC (max plot) 99.8%; Rt 4.40 min. 1H NMR (300 MHz, CDCl3) δ 11.17 (s, 1H), 8.07 (dd, J=7.9, 1.5 Hz, 1H), 7.50-7.44 (m, 1H), 7.31 (td, J=7.6, 1.3 Hz, 1H), 7.21 (dd, J=7.7, 1.3 Hz, 1H), 4.07 (s, 2H), 2.98 (d, J=6.8 Hz, 2H), 2.62 (t, J=12.7 Hz, 2H), 1.80-1.57 (m, 3H), 1.45 (s, 9H), 1.28-1.14 (m, 2H).

Workup

  1. extractionthe mixture extracted with DCM (2×)
  2. dry with materialThe combined organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cde10b5dced345b08d9f316159fbc08a
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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