Diisopropylethylamine → 4-Amino-3-methoxy-n-(1-methylpiperidin-4-yl)benzamide

HRID 2279993Notes

Reaction equation

HRID 2279993 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:44][CH:45]1[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]1>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:44][CH:45]2[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]2)=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2880572486-69-3HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27375314-Amino-1-methylpiperidine

Product 1

HCID 115290634-Amino-3-methoxy-n-(1-methylpiperidin-4-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-amino-3-methoxybenzoic acid (1.064 g mg, 6.37 mmol) in dichloromethane (50 ml) was added DIPEA (2.22 ul, 12.74 mmol) and TBTU (2.25 g, 7.0 mmol) and the mixture stirred for 10 minutes. 4-amino-1-methylpiperidine (0.872 g, 7.65 mmol) was added and stirring continued for 16 hours. The resulting solid was filtered and dried under vacuum (1.04 g, 3.95 mmol, 62%).

Workup

  1. stirringstirring
  2. waitcontinued for 16 hours
  3. filtrationThe resulting solid was filtered
  4. customdried under vacuum (1.04 g, 3.95 mmol, 62%)

Sources & evidence

ORD record
ord-36a2869a8f614637b5f9446ac76fb68e
Source dataset
uspto-grants-2015_09
Patent number
US09133199B2

Reaction notes

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