2-Nitrobenzoic acid → HCID 69510346, compound

HRID 969662Notes

Reaction equation

HRID 969662 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[CH3:13][C:14]([C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)([CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)[CH3:15].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.C(Cl)CCl>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:29][C:26]1[CH:27]=[CH:28][C:23]([C:14]([CH3:15])([CH:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)[CH3:13])=[CH:24][CH:25]=1)=[O:8])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 110872-Nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 21959569HCID 21959569, compound

Product 1

HCID 69510346HCID 69510346, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-nitrobenzoic acid (400 mg), 4-[1-methyl-1-(1-methylpiperidin-4-yl)-ethyl]phenylamine (Preparation IV (aw)) (600 mg) and DIEA (0.6 mL) in CH2Cl2 (80 mL) was added EDC (600 mg) and HOBt (350 mg). The reaction was stirred at RT overnight and washed with saturated NaHCO3 (30 mL), H2O (50 mL) and brine (30 mL). The organic layer was dried over Na2SO4 and evaporated to give 2-nitro-N-{4-[1-methyl-1-(1-methylpiperidin-4-yl)ethyl]phenyl}benzamide which was used in the next step without further purification.

Workup

  1. washwashed with saturated NaHCO3 (30 mL), H2O (50 mL) and brine (30 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-b2900203be2a4b0e9966330701f3bc6d
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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