Hydrochloric Acid → HCID 18770386, compound

HRID 479395Notes

Reaction equation

HRID 479395 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-b06c4067f2c74b0782e832c71b774576
Source dataset
uspto-grants-2003_11
Patent number
US06645957B2

Reaction notes

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