Diisopropylethylamine → 4-Iodo-3-methoxy-N-(1-methylpiperidin-yl)benzamide

HRID 81964

Reaction equation

HRID 81964 reaction equation
[I:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([O:8]OC(C)(C)C)=O)=[CH:4][C:3]=1[O:16][CH3:17].C([N:20](C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:49][N:50]1[CH2:55][CH2:54][CH:53](N)[CH2:52][CH2:51]1>CN(C)C=O.O>[I:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:20][CH:51]2[CH2:52][CH2:53][CH2:54][CH2:55][N:50]2[CH3:49])=[O:8])=[CH:4][C:3]=1[O:16][CH3:17]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27375314-Amino-1-methylpiperidineHCID 86653099tert-Butyloxy 4-Iodo-3-methoxybenzoate

Product 1

HCID 666880784-Iodo-3-methoxy-N-(1-methylpiperidin-yl)benzamideYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyloxy 4-iodo-3-methoxybenzoate (250 mg, 0.90 mmol) in anhydrous dimethylformamide (8 mL) was treated with N-ethyl-N,N-diisopropylamine (0.63 mL, 3.6 mmol) and TBTU (404 mg, 1.26 mmol). The mixture was then treated with 1-methylpiperidin-4-amine (0.160 mL, 1.26 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction was diluted with water and the resulting precipitate was collected by filtration to afford the title compound (250 mg, 71% yield).

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-0c9e7cf7d3ff4f94af6359c374cf9327
Source dataset
uspto-grants-2014_09
Patent number
US08846701B2

Linked notes

Loading…