4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-chloronitrobenzene → Tert-butyl 4-(4-amino-2-chlorophenoxy)piperidine-1-carboxylate

HRID 1268182Notes

Reaction equation

HRID 1268182 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=2[Cl:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Zn]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[Cl:24])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 221810984-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-chloronitrobenzene

Product 1

HCID 22181153Tert-butyl 4-(4-amino-2-chlorophenoxy)piperidine-1-carboxylateYield 90.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-chloronitrobenzene (2.40 g) in acetic acid (50 ml) was added zinc powder (5.60 g) in four portions at room temperature and the mixture was stirred for 2 hours. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=1/1 as an eluant to give the desired compound (1.99 g, yield 87%) as an orange oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-4467e4272f834683bbee8f9d7f40bb31
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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