Phosphorus oxychloride → HCID 59730557, compound

HRID 130363Notes

Reaction equation

HRID 130363 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][NH:18]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:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][NH:18]3)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59730550HCID 59730550, compound

Product 1

HCID 59730557HCID 59730557, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Hydroxy-4-(1-H-indol-4-yl)-piperidine-1-carboxylic acid tert-butyl ester 4-5 (1.0 g, 3.17 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 (670 mg, 71%) of 4-(1H-Indol-4-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 4-6.

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-b6e5dd78a36346ffb1ec3d41ad370d8f
Source dataset
uspto-grants-2008_06
Patent number
US07381739B2

Reaction notes

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