Hydrochloric Acid → Hydrochloric Acid

HRID 2181284Notes

Reaction equation

HRID 2181284 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[C:6]1([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)O)[CH3:3].[ClH:26].[OH-].[Na+]>>[ClH:26].[ClH:26].[CH3:25][O:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)/[CH:17]=[C:6]1/[C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[O:9][CH2:10][CH2:11][CH:5]/1[CH2:4][N:2]([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22485742HCID 22485742, compound

Product 2

HCID 313Hydrochloric AcidHCID 22485740HCID 22485740, compound

Procedure

1.00 g (4RS,5RS)-4-dimethylaminomethyl-5-(3-methoxybenzyl)-2,3,4,5-tetrahydro-benzo[b]oxepin-5-ol (see example 6) and 48 ml 6N hydrocloric acid were stirred at 20° C. for 24 h and at 50° C. for 8 h. The mixture was then rendered alkaline with 6N sodium hydroxide solution and extracted three times with 20 ml ethyl acetate each time. The extracts were washed with a saturated sodium chloride solution, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography with ethyl acetate as the eluting agent. After conversion into the hydrochloride with a solution of hydrogen chloride in diethyl ether, 0.72 g (68.6% of th.) of the title compound was obtained.

Workup

  1. extractionextracted three times with 20 ml ethyl acetate each time
  2. washThe extracts were washed with a saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography with ethyl acetate as the eluting agent

Sources & evidence

ORD record
ord-2c7a7cfcba7d4655b09bb2706e10f55b
Source dataset
uspto-grants-2005_05
Patent number
US06890952B2

Reaction notes

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