N,N-Dimethylaniline → 3,4-Difluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

HRID 1514057Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C[N:11]([CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.ClC(Cl)(O[C:23](=[O:29])OC(Cl)(Cl)Cl)Cl.[CH2:31]1COCC1>>[CH2:15]([CH:16]1[CH2:17][CH2:12][N:11]([C:23]([O:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)=[O:29])[CH2:18][CH2:31]1)[C:14]#[CH:13]

Participants

Reactant 4

HCID 949N,N-Dimethylaniline

HCID 8028Tetrahydrofuran2×

HCID 759273,4-Difluorophenol

HCID 94429Triphosgene

Product 1

HCID 578388903,4-Difluorophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Procedure

3,4-Difluoro-phenol (3.85 g, 29.6 mmol) was added as a solution in THF and dimethylaniline to a mixture of triphosgene (2.849 g, 9.6 mmol) in THF according to general procedure 3. Yield=4.6 g, 56%. m/z MH+=280.15. HPLC rt=11.88 min.

Workup

customHPLC rt=11.88 min.

Sources & evidence

ORD record: ord-2afa0f8d1d3a4ec28261a5c8ce97f48e
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222228B2

Reaction notes

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