Hydrochloric Acid → (2-{3-[2-(1-Adamantyl)ethoxy]phenyl}ethyl)amine

HRID 1925501Notes

Reaction equation

HRID 1925501 reaction equation
[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22]C(=O)OC(C)(C)C)[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl>O1CCOCC1>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH2:22])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86649160Tert-butyl (2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-carbamate

Product 1

HCID 67520349(2-{3-[2-(1-Adamantyl)ethoxy]phenyl}ethyl)amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Intermediate 30 (7 g, 17.5 mmol) in dioxane (70 mL) was added hydrogen chloride (1.25M in dioxane, 25 mL). The reaction mixture was stirred at room temperature overnight. The precipitate was filtrated and washed with dioxane and ether. The crude was purified by column chromatography with silica gel, eluting with methylen chloride/methanol/ammonium (40:4:0.2) and the title compound was obtained as an oil (2.6 g, 50%). (M+): 300.

Workup

  1. filtrationThe precipitate was filtrated
  2. washwashed with dioxane and ether
  3. customThe crude was purified by column chromatography with silica gel
  4. washeluting with methylen chloride/methanol/ammonium (40:4:0.2)

Sources & evidence

ORD record
ord-2a95a74d120e4f67840889e577092058
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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