Hydrochloric Acid → HCID 18770386, compound

HRID 1279438Notes

Reaction equation

HRID 1279438 reaction equation
[ClH:1].C(OCC)(=O)C.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH:29]3[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]3)[CH2:24][CH2:23]2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[ClH:1].[ClH:1].[ClH:1].[ClH:1].[NH:32]1[CH2:33][CH2:34][CH:29]([CH2:28][N:25]2[CH2:24][CH2:23][N:22]([CH2:21][CH:18]3[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)[CH2:27][CH2:26]2)[CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 187704261,4-Bis[(1-tert-butoxycarbonyl-4-piperidinyl)methyl]piperazine

Product 1

HCID 18770386HCID 18770386, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4N hydrogen chloride in ethyl acetate (4 ml; 16 mmol) was added to a solution in methylene chloride (2 ml) of 1,4-bis[(1-tert-butoxycarbonyl-4-piperidinyl)methyl]-piperazine (195 mg; 0.40 mmol) synthesized by the above process under ice cooling, and the mixture was stirred for 30 minutes. The ice bath was removed, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure, and the resultant crude crystals were recrystallized from methylene chloride-methanol-diethyl ether, thereby obtaining 154 mg (yield: 84%) of the title compound as a colorless crystalline powder (melting point: 280° C. or higher).

Workup

  1. customsynthesized by the above process under ice cooling
  2. customThe ice bath was removed
  3. stirringthe mixture was stirred at room temperature for 12 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe resultant crude crystals were recrystallized from methylene chloride-methanol-diethyl ether

Sources & evidence

ORD record
ord-5ad890fbd0d0425eb7193850281ddaac
Source dataset
uspto-grants-2002_09
Patent number
US06448242B1

Reaction notes

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