Hydrochloric Acid → HCID 15023452, compound

HRID 973982Notes

Reaction equation

HRID 973982 reaction equation
[Cl:1][C:2]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].Cl.[NH2:19][CH2:20][C:21]#[C:22][CH2:23][OH:24].C(N(CC)CC)C.Cl>C(Cl)Cl>[OH:24][CH2:23][C:22]#[C:21][CH2:20][NH:19][C:3](=[O:4])[C:2]([Cl:1])([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 197755142-Chloro-2-cyclohexyl-2-phenylacetyl chlorideHCID 197755314-Aminobut-2-yn-1-ol hydrochloride

Product 1

HCID 15023452HCID 15023452, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-chloro-2-cyclohexyl-2-phenylacetyl chloride (9.0 g) in methylene chloride (50 ml) was added dropwise to a solution of 4-amino-2-butyn-1-ol hydrochloride (5.38 g) and triethylamine (30.8 ml) in methylene chloride (120 ml) at 0° C. The mixture was stirred at the same temperature for 10 minutes and then at room temperature for an additional 3.5 hours and 1N hydrochloric acid was added thereto. The organic layer was separated, washed with saturated sodium bicarbonate, aqueous solution, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and ethyl acetate (6:1) as an eluent to give N-(4-hydroxy-2-butynyl)-2-chloro-2-cyclohexyl-2-phenylacetamide (7.32 g).

Workup

  1. waitat room temperature for an additional 3.5 hours
  2. customThe organic layer was separated
  3. washwashed with saturated sodium bicarbonate, aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and ethyl acetate (6:1) as an eluent

Sources & evidence

ORD record
ord-afbc94e874404c8e95c578c3f25c762e
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Reaction notes

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