Sodium Hydroxide → HCID 54429783, compound

HRID 376785Notes

Reaction equation

HRID 376785 reaction equation
[N:1]([C:4]1[C:11]([F:12])=[C:10]([F:13])[C:7]([CH:8]=O)=[C:6]([F:14])[C:5]=1[F:15])=[N+:2]=[N-:3].[CH3:16][N:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1.[OH-].[Na+]>CO.O>[N:1]([C:4]1[C:11]([F:12])=[C:10]([F:13])[C:7]([CH:8]=[C:19]2[C:20](=[O:23])[C:21](=[CH:8][C:7]3[C:6]([F:14])=[C:5]([F:15])[C:4]([N:1]=[N+:2]=[N-:3])=[C:11]([F:12])[C:10]=3[F:13])[CH2:22][N:17]([CH3:16])[CH2:18]2)=[C:6]([F:14])[C:5]=1[F:15])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 740491-Methyl-4-piperidoneHCID 11020377HCID 11020377, compound

Product 1

HCID 54429783HCID 54429783, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 4-azido-2,3,5,6-tetrafluorobenzaldehyde (23), 0.140 g, 0.640 mmol) and 1-methylpiperidine-4-one (0.040 mL, 0.32 mmol) in MeOH (1.5 mL), 1N aq. NaOH (0.650 mL, 0.650 mmol) was added dropwise. Yellow suspension resulted within minutes which was stirred at rt for forty-five minutes and diluted with water (3 mL). Yellow solid was collected by vacuum filtration, washed with water until the filtrate was neutral to pH paper. The yellow solid was dried further in vacuo to give 0.139 g (83%) 3,5-bis(4'-azido-2',3',5',6'-tetrafluorophenylmethylene)-1-methyl piperidine-4-one (22) as bright yellow powder; mp 153° C. (violent decomposition). 1HNMR(CDCL3 δ 2.37 (s, 3H), 3.42 (s, 4H), 7.55 (s,2H). ##STR28##

Workup

  1. customYellow suspension resulted within minutes which
  2. filtrationYellow solid was collected by vacuum filtration
  3. washwashed with water until the filtrate
  4. customThe yellow solid was dried further in vacuo

Sources & evidence

ORD record
ord-f83a8f8077a5475c9a614f92b75d4ab6
Source dataset
uspto-grants-2000_02
Patent number
US06022597

Reaction notes

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