Methoxyacetyl chloride → methoxyacetic acid N-(1-Boc-piperidin-3-ylmethyl)-N-phenylamide

HRID 1246899Notes

Reaction equation

HRID 1246899 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:22][O:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:25](=[O:26])[CH2:24][O:23][CH3:22])[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 12972131N-(1-Boc-piperidin-3-ylmethyl)aniline

Product 1

HCID 53812669methoxyacetic acid N-(1-Boc-piperidin-3-ylmethyl)-N-phenylamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of N-(1-Boc-piperidin-3-ylmethyl)-aniline 4 (101 mg, 0.348 mmol) and piperidinomethyl polystyrene resin (110 mg) in 2 mL of dry CH2Cl2 was added methoxyacetyl chloride (97%, 34 μL, 1.05 eq.) at room temperature. After being shaken at room temperature for 4 hours, the reaction mixture was passed through an aminopropyl NH2 cartridge and washed with CH2Cl2 Removal of CH2Cl2 afforded methoxyacetic acid N-(1-Boc-piperidin-3-ylmethyl)-N-phenylamide 38 (70 mg, 56%).

Workup

  1. washwashed with CH2Cl2 Removal of CH2Cl2

Sources & evidence

ORD record
ord-01b1205dff574476b684cbc3acb810e2
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Reaction notes

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