Acetic Acid → HCID 15251992, compound

HRID 2120085Notes

Reaction equation

HRID 2120085 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1)(OC(C)(C)C)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>C(Cl)Cl>[N:1]1([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4837PiperazineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15251992HCID 15251992, compoundYield 225.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step 4 (1.9 g, 5.79 mmol), N-BOC-4-piperidone (5.73 g, 28.8 mmol), NaBH(OAc)3 (6.1 g, 28.8 mmol) and 2M AcOH (5.76 ml, 11.52 mmol) were combined in CH2Cl2 (150 ml) and the mixture was stirred overnight. After the solvent was removed, NaOH (3N) was added and extractive work up with EtOAc followed by silica gel chromatography afforded pure piperazino-piperidine (2.21 g, 75% yield, Rf=0.18, hexanes/EtOAc, 1:1) as a syrup.

Workup

  1. customAfter the solvent was removed
  2. additionNaOH (3N) was added

Sources & evidence

ORD record
ord-c43472a2b2504412939feb9285a05fe2
Source dataset
uspto-grants-2004_02
Patent number
US06689765B2

Reaction notes

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