Aniline → HCID 86599752, compound

HRID 1393919Notes

Reaction equation

HRID 1393919 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]1=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:19](Cl)(Cl)(Cl)=[O:20].[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([P:19]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:20])[C:13]1=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 24813Phosphorus oxychlorideHCID 11482034Benzyl [(3S)-2-oxopiperidin-3-yl]carbamate

Product 1

HCID 86599752HCID 86599752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (3S)-3-benzyloxycarbonylamino-2-piperidone (2.48 g, 9.99 mmol) in tetrahydrofuran (30 mL) was cooled at an external temperature of −78° C., followed by adding dropwise thereto an n-butyllithium-hexane solution (1.50 M, 6.5 mL, 9.75 mmol) over a period of 20 minutes, and the resulting mixture was stirred at the same temperature for 30 minutes. Subsequently, a solution of phosphorus oxychloride (1.53 g, 9.98 mmol) in tetrahydrofuran (3 mL) was added thereto and stirred for 20 minutes, after which aniline (d=1.022, 4.1 mL, 44.99 mmol) was added thereto and stirred for 1.5 hours.

Workup

  1. additionby adding dropwise
  2. stirringstirred for 20 minutes
  3. stirringstirred for 1.5 hours

Sources & evidence

ORD record
ord-8bd686bdea454496b3d0ca688af5f1ec
Source dataset
uspto-grants-2008_03
Patent number
US07348318B2

Reaction notes

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