Hydrochloric Acid → HCID 86738353, compound

HRID 2286199Notes

Reaction equation

HRID 2286199 reaction equation
[NH2:1][C:2]1[C:20]([NH2:21])=[CH:19][C:5]2[O:6][C:7]([CH3:18])([CH3:17])[C@@H:8]([OH:16])[C@H:9]([N:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[C:4]=2[CH:3]=1.Cl.[C:23](Cl)([Cl:25])=[O:24]>C1(C)C=CC=CC=1>[ClH:25].[OH:16][C@@H:8]1[C:7]([CH3:17])([CH3:18])[O:6][C:5]2=[CH:19][C:20]3[NH:21][C:23](=[O:24])[NH:1][C:2]=3[CH:3]=[C:4]2[C@H:9]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 14674145HCID 14674145, compound

Product 1

HCID 86738353HCID 86738353, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 6,7-diamino-3,4-dihydro-2,2-dimethyl-trans-4-piperidino-2H-benzo[b]pyran-3-ol (0.12 g) in 5N-hydrochloric acid (10 ml) was treated with a 12.5% solution of phosgene in toluene (20 ml) and the mixture was stirred at room temperature for 45 minutes. A vigorous stream of nitrogen was then passed through the mixture for 10 minutes, and the solution was evaporated to dryness in vacuo. The residue was recrystallised from ethanol-ether to give the hygroscopic 3,6,7,8-tetrahydro-trans-7-hydroxy-6,6-dimethyl-8-piperidino-pyrano[2,3-f]benzimidazole-2 (1H)-one hydrochloride (1) (0.067 g) mp 177°-180° C.

Workup

  1. waitA vigorous stream of nitrogen was then passed through the mixture for 10 minutes
  2. customthe solution was evaporated to dryness in vacuo
  3. customThe residue was recrystallised from ethanol-ether

Sources & evidence

ORD record
ord-69eb620a40754a81a4792deec185e610
Source dataset
uspto-grants-1982_04
Patent number
US04327099

Reaction notes

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