Hydrochloric Acid → HCID 70874117, compound

HRID 2208847Notes

Reaction equation

HRID 2208847 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:25]([O:27]C)=[O:26])[C:5]([CH3:24])=[C:6]([N:8]([CH2:22][CH3:23])[CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.[Li+].[OH-].[OH-].[Na+].Cl>O1CCCC1.O>[C:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][CH:9]([N:8]([CH2:22][CH3:23])[C:6]2[C:5]([CH3:24])=[C:4]([CH:3]=[C:2]([Cl:1])[CH:7]=2)[C:25]([OH:27])=[O:26])[CH2:14][CH2:13]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 86719534HCID 86719534, compound

Product 1

HCID 70874117HCID 70874117, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-{[5-chloro-3-(methoxycarbonyl)-2-methylphenyl](ethyl)amino}piperidine-1-carboxylate (131 mg, 0.32 mmol) in tetrahydrofuran (2 ml) was added LiOH (8.4 mg, 0.35 mmol) in deionized water (2 ml). The reaction mixture was stirred in air at room temperature for 24 hours. 1M NaOH (3.19 ml) was added to the reaction mixture and this was stirred for a further 24 hours. The reaction mixture was then warmed to 40° C. for 25 h. The reaction mixture was acidified to pH 2-3 with 1M HCl and extracted with EtOAc (3×20 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give 122 mg of the title compound as a thick orange oil. LC-MS 76%, m/z=397.5/399.4, 1H NMR (500 MHz, Chloroform-d) δ ppm 7.74 (1H, s), 7.20-7.35 (2H, m), 3.92-4.11 (2H, m), 2.97-3.13 (2H, m), 2.81-2.95 (1H, m), 2.62-2.79 (2H, m), 2.53 (3H, s), 1.75 (2H, br. s.), 1.48-1.61 (2H, m), 1.46 (9H, s), 0.89 (3H, t, J=6.86 Hz).

Workup

  1. stirringthis was stirred for a further 24 hours
  2. temperatureThe reaction mixture was then warmed to 40° C. for 25 h
  3. extractionextracted with EtOAc (3×20 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03140617f9854c1692f4c9cdfa302348
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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