Sodium Hydroxide → HCID 14153817, compound

HRID 1253002Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred suspension of 6.7 g (0.168 mole) of 60% sodium hydride/mineral oil in 500 ml of dimethylsulfoxide was added 50 g (0.168 mole) of 2-chloro-N-(4-hydroxy-1-methyl-4-piperidinylmethyl)-N-methyl-3-pyridinecarboxamide and the mixture was heated to 70° C. for 20 hr. An equal volume of dilute sodium hydroxide was added and the solution was extracted twice with methylene chloride. The combined methylene chloride solution was extracted 3 times with water followed by 3 extractions with dilute hydrochloric acid. The acid layers were combined, made basic with concentrated sodium hydroxide, and extracted 3 times with methylene chloride. The combined methylene chloride extract was dried over sodium sulfate and concentrated. Yield of residue was 23 g (52%).

Workup

extractionthe solution was extracted twice with methylene chloride
extractionThe combined methylene chloride solution was extracted 3 times with water
extractionfollowed by 3 extractions with dilute hydrochloric acid
extractionextracted 3 times with methylene chloride
extractionThe combined methylene chloride extract
dry with materialwas dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-14ef402cab5a44b58462486cba137624
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04746655

Reaction notes

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