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1-Phenylpiperazine → HCID 178453926, compound

HRID 1600684
Notes
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Reaction equation

HRID 1600684 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:26]1([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][C:16](=[O:18])[N:35]2[CH2:36][CH2:37][N:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:33][CH2:34]2)[CH2:13][CH2:14]1)([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 178453927HCID 178453927, compound

Product 1

HCID 178453926HCID 178453926, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a colution containing trans-(4-tertbutoxycarbonylamino-cyclohexyl)-acetic acid (15.44 g, 0.06 mol), triethylamine (6.05 g, 0.06 mol) and 1-phenylpiperazine (9.73 g, 0.06 mol) in CH2Cl2 (250 mL) was added EDAC-HCl ((1-ethyl-(3dimethylaminopropyl)-carbodiimide hydrochloride (11.5 g, 0.06 mol)). The reaction mixture was stirred at room temperature 16 hours, then washed with water, 1N NaOH, brine, and dried (MgSO4). The solvent was evaporated, and the residue was chromatographed on a flash silica gel column eluting with CH2Cl2 and then EtOAc. The product fractions were recrystallized from acetonitrile (CH3CN) to yield 12.0 g (50%) of trans-{4-[2-oxo-2-(4-phenyl-piperazin-1-yl)-ethyl]-cylohexyl}-carbamic acid tert-butyl ester as white crystals; mp 197.5-200° C.

Workup

  1. washwashed with water, 1N NaOH, brine
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed on a flash silica gel column
  5. washeluting with CH2Cl2
  6. customThe product fractions were recrystallized from acetonitrile (CH3CN)

Sources & evidence

ORD record
ord-f1ba7317f738441daa16e291bb3b3355
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05977110

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes