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Hydrochloric Acid → 3-[4-(2-Oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-benzoic acid

HRID 74501
Notes
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Reaction equation

HRID 74501 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=3)[C:18]([O:20]CC)=[O:19])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=2[NH:3]1.[OH-].[Na+].Cl>C1COCC1.O>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=3)[C:18]([OH:20])=[O:19])[CH2:13][CH2:14]2)[CH2:7][CH2:6][C:5]2[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=2[NH:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58386382HCID 58386382, compound

Product 1

HCID 583866643-[4-(2-Oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

650 mg (1.65 mmol) ethyl 3-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-benzoate, 10 mL THF, 2 mL water and 2 mL (8.00 mmol) of an aqueous 4M sodium hydroxide solution were stirred at RT until the reaction was complete. Then the THF was eliminated i. vac. The aqueous residue was acidified with a 4M hydrochloric acid solution. After several hours' stirring at RT the precipitate was suction filtered and dried.

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-0b3c37f68d9c404d8649521712623393
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829006B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes