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

HRID 1619095Notes

Reaction equation

HRID 1619095 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].C([N:15](C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:44][N:45]1[CH2:50][CH2:49][CH:48](N)[CH2:47][CH2:46]1>CN(C)C=O.O>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:15][CH:46]2[CH2:47][CH2:48][CH2:49][CH2:50][N:45]2[CH3:44])=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27375314-Amino-1-methylpiperidineHCID 179342274-Iodo-3-methoxybenzoic acid

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 4-iodo-3-methoxybenzoic acid (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 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-9720c5317ea147958e81fe8fc8be1d33
Source dataset
uspto-grants-2014_07
Patent number
US08772280B2

Reaction notes

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