Sodium Hydroxide → 4-(3,4-Dichlorophenoxy)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

HRID 1070911Notes

Reaction equation

HRID 1070911 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[Cl:15])[O:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[C:16]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>ClCCCl.C(OCC)C.C(O)(=O)C>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][CH:26]([N:9]2[CH2:10][CH2:11][CH:6]([O:5][C:4]3[CH:12]=[CH:13][C:14]([Cl:15])=[C:2]([Cl:1])[CH:3]=3)[CH2:7][CH2:8]2)[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 37320424-(3,4-Dichlorophenoxy)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 112125444-(3,4-Dichlorophenoxy)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

4-(3,4-Dichlorophenoxy)piperidine (1.5 g) was dissolved in 1,2-dichloroethane (21 ml). 1-Boc-4-piperidone was added (1.21 g) followed by NaBH(OAc)3 (1.81 g) and acetic acid (0.37 g). After 18 hours at room temperature aqueous NaOH (1M) solution and diethyl ether were added. The product was extracted with diethyl ether, the combined organic extracts dried with MgSO4 and concentrated. Purification by silica chromatography (dichloromethane:methanol 92:8) gave the sub-title product (1.97 g).

Workup

  1. extractionThe product was extracted with diethyl ether
  2. dry with materialthe combined organic extracts dried with MgSO4
  3. concentrationconcentrated
  4. customPurification by silica chromatography (dichloromethane:methanol 92:8)

Sources & evidence

ORD record
ord-21b5084962d44a2e9c904bebc91780db
Source dataset
uspto-grants-2005_06
Patent number
US06903115B2

Reaction notes

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