Hydrochloric Acid → HCID 18007237, compound

HRID 2299614Notes

Reaction equation

HRID 2299614 reaction equation
[CH2:1]([N:8](C(OC(C)(C)C)=O)[CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[C:17]([OH:21])[C:18]([Cl:20])=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(OCC)(=O)C>[CH2:1]([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[C:17]([OH:21])[C:18]([Cl:20])=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53886401HCID 53886401, compound

Product 1

HCID 18007237HCID 18007237, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-benzyl-N-(3-chloro-6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl)-tert-butoxycarbonylamine (135 mg) and 4N hydrogen chloride in ethyl acetate (3 ml) was stirred under ice-cooling for 2 hours and at room temperature for 5 hours and evaporated in vacuo. The residue was partitioned between ethyl acetate and an aqueous solution of sodium bicarbonate. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo to afford N-benzyl-(3-chloro-6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl)amine (100 mg) as a yellow gum.

Workup

  1. customevaporated in vacuo
  2. customThe residue was partitioned between ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b74d2d6eab0448ad97ad5a9f131b3eae
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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