Hydrochloric Acid → N-[(1S,2S)-2-Aminocyclopentyl]-2-chlorobenzamide hydrochloride

HRID 1750491Notes

Reaction equation

HRID 1750491 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])OC(C)(C)C.C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1C(Cl)=O.Cl.O1CCOCC1>C(Cl)Cl>[ClH:22].[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[Cl:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 691102-Chlorobenzoyl chlorideHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamine

Product 1

HCID 118308080N-[(1S,2S)-2-Aminocyclopentyl]-2-chlorobenzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 500 mg, 2.497 mmol) in dry DCM (8.3 ml) was added triethylamine (1.74 ml, 12.48 mmol) and 2-chlorobenzoyl chloride (CAS number 609-65-4; 476 μl, 3.74 mmol). The reaction was stirred at room temperature for 72 hours. The reaction was partitioned between DCM and a saturated solution of sodium bicarbonate, filtered through a hydrophobic frit and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol). The Boc protect intermediate was dissolved in 1,4-dioxane (8 ml) and to this was added HCl in 1,4-dioxane (4 M, 6.0 ml, 23.91 mmol). The reaction was stirred at room temperature for 17 hours and then concentrated in vacuo, azeotropically distilled with toluene to afford the title compound.

Workup

  1. customThe reaction was partitioned between DCM
  2. filtrationa saturated solution of sodium bicarbonate, filtered through a hydrophobic frit
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol)
  5. dissolutionwas dissolved in 1,4-dioxane (8 ml)
  6. stirringThe reaction was stirred at room temperature for 17 hours
  7. concentrationconcentrated in vacuo
  8. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-1911af571c03439eb4e733607a58d066
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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