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Trifluoroacetic acid → 1-[1-(3-Methoxy-4-nitrophenyl)piperidin-4-yl]-4-methyl-1,4-azaphosphinane 4-oxide

HRID 1472023
Notes
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Reaction equation

HRID 1472023 reaction equation
[CH3:1][P:2]1(=[O:21])[CH2:7][CH2:6][N:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+].FC1[CH:37]=[CH:38][C:39]([N+:44]([O-:46])=[O:45])=[C:40]([O:42][CH3:43])[CH:41]=1>C(Cl)Cl>[CH3:43][O:42][C:40]1[CH:41]=[C:14]([N:11]2[CH2:10][CH2:9][CH:8]([N:5]3[CH2:4][CH2:3][P:2](=[O:21])([CH3:1])[CH2:7][CH2:6]3)[CH2:13][CH2:12]2)[CH:37]=[CH:38][C:39]=1[N+:44]([O-:46])=[O:45]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisoleHCID 67052687Tert-butyl 4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidine-1-carboxylate

Product 1

HCID 681570431-[1-(3-Methoxy-4-nitrophenyl)piperidin-4-yl]-4-methyl-1,4-azaphosphinane 4-oxideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of tert-butyl 4-(4-methyl-4-oxido-1,4-azaphosphinan-1-yl)piperidine-1-carboxylate (178 mg, 0.563 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (0.5 mL). After 20 min, the solution was concentrated and the resulting residue was redissolved in DMF (2 mL). Potassium carbonate (160 mg, 1.16 mmol) was added portionwise to the stirring solution followed by 5-fluoro-2-nitroanisole (158 mg, 0.930 mmol). The reaction mixture was heated to 50° C. After 2 h, the reaction mixture was concentrated and the residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane) to afford the compound as a bright yellow solid (176 mg, 86% yield).

Workup

  1. concentrationthe solution was concentrated
  2. dissolutionthe resulting residue was redissolved in DMF (2 mL)
  3. waitAfter 2 h
  4. concentrationthe reaction mixture was concentrated
  5. customthe residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane)

Sources & evidence

ORD record
ord-614440badf914e1d80c551b808644c46
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012462B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes