Phosphoric Acid → HCID 17980119, compound

HRID 1766222Notes

Reaction equation

HRID 1766222 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH2:13][CH2:14][C:7]3=[CH:6][C:5]=2[CH:4]=1.OP(O)(O)=O.[CH3:20][N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1.[OH-].[NH4+]>CC(O)=O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH2:13][CH2:14][C:7]3=[C:6]([C:24]3[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH:23]=3)[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 14923Ammonium HydroxideHCID 740491-Methyl-4-piperidoneHCID 17980109HCID 17980109, compound

Product 1

HCID 17980119HCID 17980119, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-methoxy-2,3-dihydro-1H-pyrrolo[1,2-a]indole (718 mg, 3.83 mmol) (Clark, R. D.; Muchowski, J. M.; Fisher, L. E.; Flippen, L. A.; Repke, D. B.; Souchet, M. Synthesis 10,871-878(1991); Ishikura, M.; Terashima, M. Tetrahedron Lett. 33, 6849-6852(1992)) in glacial AcOH (20 mL) at 60° C. was added H3PO4 (5.0 mL, 10 mmol, 2.0 N) and 1-methyl-4-piperidone (1.2 mL, 11.5 mmol). The reaction was heated for 1 h at 60° C., cooled to room temperature and poured into a mixture of ammonium hydroxide in ice water. This reaction mixture was extracted with ethyl acetate and washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure yielded 1.07 g (99%) of the title compound as a brown oil: MS (ES+): m/e 283.0 (M+1).

Workup

  1. customSynthesis 10,871-878(1991)
  2. temperaturecooled to room temperature
  3. extractionThis reaction mixture was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f24bc7f7eea4cc1acbe8dd948aebc3e
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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