Phosphorus oxychloride → HCID 60108780, compound

HRID 1296582Notes

Reaction equation

HRID 1296582 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[CH:19]3)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 60108792HCID 60108792, compound

Product 1

HCID 60108780HCID 60108780, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Hydroxy-4-(1-H-indol-7-yl)-piperidine-1-carboxylic acid tert-butyl ester XVI (1.17 g, 3.7 mmol) was combined with pyridine (20 mL) and phosphorus oxychloride (0.7 mL, 7.4 mmol) at room temperature under nitrogen, and was stirred overnight. The reaction was partitioned between ethyl acetate (55 mL) and water (55 mL). The ethyl acetate layer was washed with water (2×30 mL) and brine (55 mL), then dried (MgSO4), filtered and concentrated to afford (700 mg, 64%) of 4-(1H-indol-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester XVII.

Workup

  1. customThe reaction was partitioned between ethyl acetate (55 mL) and water (55 mL)
  2. washThe ethyl acetate layer was washed with water (2×30 mL) and brine (55 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-63ecb31433234779858df98efec83f99
Source dataset
uspto-grants-2007_07
Patent number
US07247651B2

Reaction notes

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