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

HRID 732901

Reaction equation

HRID 732901 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].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:3]2[CH:4]=[CH:5][C:6]([Br:8])=[CH:7][C:2]=2[Br:1])=[O:29])[CH2:18][CH2:31]1)[C:14]#[CH:13]

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 8028Tetrahydrofuran2×HCID 120052,4-DibromophenolHCID 94429Triphosgene

Product 1

HCID 578389122,4-Dibromophenyl 4-(prop-2-ynyl)piperidine-1-carboxylate

Procedure

2,4-Dibromophenol (7.45 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=6.09 g, 68%. m/z MH+=402.22. HPLC rt=12.49 min.

Workup

  1. customHPLC rt=12.49 min.

Sources & evidence

ORD record
ord-c035ca37c20646abba2c8df2711900b0
Source dataset
uspto-grants-2009_09
Patent number
US07589076B2

Linked notes

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