Thionyl Chloride → 2-methoxy-4-(1-Boc-4-piperidyloxy)benzoyl chloride

HRID 128589Notes

Reaction equation

HRID 128589 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].S(Cl)([Cl:28])=O>C1COCC1.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH:9]=[CH:8][C:4]=1[C:5]([Cl:28])=[O:6]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 105458744-((1-(Tert-butoxycarbonyl)piperidin-4-YL)oxy)-2-methoxybenzoic acid

Product 1

HCID 189141552-methoxy-4-(1-Boc-4-piperidyloxy)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxy-4-(1-Boc-4-piperidyloxy)benzoic acid (3.2 g, 9.1 mmol) was dissolved in THF (35 ml). Thionyl chloride (1 ml, 1.63 g, 13.7 mmol) was added dropwise, followed by 2 drops of pyridine. The mixture was stirred at ambient temperature under nitrogen for 4.5 hours, then concentrated in vacuo. The residue was reconcentrated from ether to give 2-methoxy-4-(1-Boc-4-piperidyloxy)benzoyl chloride.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9da396479ca493d98c201b4fcb0b532
Source dataset
uspto-grants-1995_11
Patent number
US05464788

Reaction notes

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