Phosphoric Acid → HCID 10826203, compound

HRID 429185Notes

Reaction equation

HRID 429185 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.Cl.[NH:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.P(=O)(O)(O)O.CCOC(C)=O>CC(O)=O>[NH:18]1[CH2:19][CH:20]=[C:21]([C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 8857Ethyl AcetateHCID 136982-PhenylindoleHCID 2723901Piperonylamine

Product 1

HCID 10826203HCID 10826203, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Phenylindole (25 g, 130 mmol) was stirred at 80° C. in AcOH (200 ml), and 4-piperidone hydrochloride hydrate (50 g, 376 mmol) and 1M phosphoric acid (100 ml) added. After a further 6 h, the mixture was poured into ice/ammonia, and extracted with EtOAc (3×200 ml). The combined organic layers were washed with water and brine, dried, and evaporated in vacuo to give a pale yellow solid. This was suspended in boiling EtOAc (200 ml), cooled to room temperature overnight, and the solid collected, washed with EtOAc and dried to give the title compound (26 g, 73%) as a pale yellow solid; δH (360 MHz, d6-DMSO) 2.00-2.10 (2H, m, NCH2CH2), 2.89 (2H, t, J 5, NCH2CH2), 3.40-3.45 (2H, m, NCH2CH), 5.78 (1H, br s, NCH2CH), 7.00 (1H, t, J 7, indole-H), 7.08 (1H, t, J 7, indole-H), 7.20-7.50 (5H, m, ArH), 7.69 (2H, d, J 7, ArH), 11.3 (1H, br s, indole NH); m/z (ES+) 275 (M++H).

Workup

  1. extractionextracted with EtOAc (3×200 ml)
  2. washThe combined organic layers were washed with water and brine
  3. customdried
  4. customevaporated in vacuo
  5. customto give a pale yellow solid
  6. customthe solid collected
  7. washwashed with EtOAc
  8. customdried

Sources & evidence

ORD record
ord-ab74bb7587474af4b762f8fb0662cf66
Source dataset
uspto-grants-2001_11
Patent number
US06316468B1

Reaction notes

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