Thionyl Chloride → HCID 18700132, compound

HRID 1377707Notes

Reaction equation

HRID 1377707 reaction equation
[CH3:1][O:2][C:3]1[C:11]([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:10][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[C:11]([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:10][CH:9]=[CH:8][C:4]=1[C:5]([Cl:28])=[O:6]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 18700181HCID 18700181, compound

Product 1

HCID 18700132HCID 18700132, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methoxy-(N-t-butyloxycarbonyl-4-piperidyloxy)benzoic acid (3.2 g; 9.1 mmol) from Step 3 of Example 25 in THF was added thionyl chloride (1 mL; 13.7 mmol) and pyridine (2 drops) while under a nitrogen atmosphere. The solution was stirred for 4 hours and then concentrated under reduced pressure to dryness. The residue was suspended in ether and filtered, and the filtrate was concentrated to dryness to yield 2-methoxy-(N-t-butyloxycarbonyl-4-piperidyloxy)benzoyl chloride.

Workup

  1. concentrationconcentrated under reduced pressure to dryness
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-b2035ed786c841ddaaa83693d093dabc
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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