3,4-Dichloroaniline → 1-Boc-4-[(3,4-dichlorophenyl)amino]-piperidine

HRID 1059022Notes

Reaction equation

HRID 1059022 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C.CCOCC.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH:5][CH:20]1[CH2:21][CH2:22][N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH2:18][CH2:19]1

Participants

8

Reactant 4

HCID 72573,4-DichloroanilineHCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 223224131-Boc-4-[(3,4-dichlorophenyl)amino]-piperidine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 3,4-dichloroaniline (5 g), N-tert-butoxycarbonyl4-piperidone (11.7 g), sodium triacetoxyborohydride (19.7 g) and acetic acid (7 ml) in dichloroethane (150 ml) was stirred for 16 hours. 2M NaOH solution and ether were added, the organic phase separated, dried and concentrated. The residue was triturated under an isohexane:ethyl acetate, 4:1 mixture and the sub-titled product collected as a solid (7.25 g).

Workup

  1. customthe organic phase separated
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was triturated under an isohexane
  5. customethyl acetate, 4:1 mixture and the sub-titled product collected as a solid (7.25 g)

Sources & evidence

ORD record
ord-c4e1fbe14b204ac69db0593b9a0c72cc
Source dataset
uspto-grants-2003_02
Patent number
US06518286B1

Reaction notes

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