1-Phenylpiperazine → HCID 68682718, compound

HRID 1477404Notes

Reaction equation

HRID 1477404 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[C@@H:18]([C:19]([OH:21])=O)[CH2:17][CH2:16][C:13]2([CH2:15][CH2:14]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:22]1([N:28]2[CH2:33][CH2:32][N:31]([C:19]([C@H:18]3[CH2:17][CH2:16][C:13]4([CH2:15][CH2:14]4)[CH2:12][C@@H:11]3[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])=[O:21])[CH2:30][CH2:29]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67007024HCID 67007024, compound

Product 1

HCID 68682718HCID 68682718, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(5S,6S)-5-((benzyloxy)carbonyl)spiro(2,5)octane-6-carboxylic acid from step 7 (47 mg, 0.16 mmole) was dissolved in DMF (0.7 mL). To the solution, 1-phenylpiperazine (29 mg, 0.18 mmole) was added, followed by BOP (76 mg, 0.17 mmole). DIEA (53 mg, 0.41 mmole) was added after the mixture was stirred at r.t. for 10 min. The mixture was then stirred at r.t. overnight and quenched with sat'd NaHCO3 solution, extracted with EtOAc. The extract was washed with NaHCO3 sat'd solution, brine; dried over MgSO4. After filtration, the filtrate was concentrated. The resulting residue was purified by column chromatography to afford Benzyl(5S,6S)-6-((4-phenylpiperazin-1-yl)carbonyl)spiro(2.5)octane-5-carboxylate.

Workup

  1. stirringThe mixture was then stirred at r.t. overnight
  2. customquenched with sat'd NaHCO3 solution
  3. extractionextracted with EtOAc
  4. washThe extract was washed with NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-6e2bb3ebbdd5406eac12567caf215d6c
Source dataset
uspto-grants-2016_08
Patent number
US09403775B2

Reaction notes

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