Tetrahydrofuran → HCID 20381779, compound

HRID 1448054Notes

Reaction equation

HRID 1448054 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]2[C:13]3[C:18]([NH:19][C:4]=2[C:3]1=[O:20])=[CH:17][CH:16]=[CH:15][CH:14]=3.[H-].[Na+].C1COCC1.[Cl:28][CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>Cl>[ClH:28].[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]2[C:13]3[C:18]([N:19]([CH2:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)[C:4]=2[C:3]1=[O:20])=[CH:17][CH:16]=[CH:15][CH:14]=3

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 54128793HCID 54128793, compound

Product 1

HCID 20381779HCID 20381779, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1.8 g of 7-methyl-7H-indolo [3,2-b][1,5]benzoxazepin-6(5H)-one, 0.42 g of 57% sodium hydride-mineral oil dispersion and 10 ml of THF was refluxed for 15 min. and then treated with 4.0 g of 3-chloropropylpiperidine. The mixture was refluxed for 24 hrs., diluted with 2 N HCl and extracted with ether. The aqueous layer was made basic with 5% NaOH and the oil extracted with ether. The ether phase was dried and treated with dry HCl to give a white solid. The solid was recrystallized from methanol-ether to give analytical material, mp. 205°-6°.

Workup

  1. temperaturewas refluxed for 15 min.
  2. temperatureThe mixture was refluxed for 24 hrs
  3. extractionextracted with ether
  4. extractionthe oil extracted with ether
  5. dry with materialThe ether phase was dried
  6. additiontreated with dry HCl
  7. customto give a white solid
  8. customThe solid was recrystallized from methanol-ether
  9. customto give analytical material, mp. 205°-6°

Sources & evidence

ORD record
ord-0d1643dac73045dca4e6865d5b5e536b
Source dataset
uspto-grants-1979_12
Patent number
US04179513

Reaction notes

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