1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 54562765, compound

HRID 362920Notes

Reaction equation

HRID 362920 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:18]1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:15][N:2]([CH3:1])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([CH:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:19][CH2:18]2)=[O:9])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 128755351-(Diphenylmethyl)-4-piperidinamineHCID 54252267HCID 54252267, compound

Product 1

HCID 54562765HCID 54562765, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Step 3): The mixture of 4-dimethylamino-2-nitrobenzoic acid (4.20 g, 20 mmol), 4-amino-1-diphenylmethylpiperidine (5.33 g, 20 mmol). EDCl (4.00 g, 21 mmol) and DMAP (2.45 g, 20 mmol) in CH2Cl2 (60 ml) was stirred at room temperature for 17.5 hours. The reaction mixture was diluted with CH2Cl2, washed with H2O and brine. The organic layer was dried over MgSO4 and concentrated under vacuum. The residue was purified with chromatography on SiO2 (50% AcOEt in hexane) and recrystallized from AcOEt to obtain 4-dimethylamino-2-nitro-N-(1-diphenylmethylpiperidin-4-yl)benzamide. 5.44 g (59%): mp 183° C.

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified with chromatography on SiO2 (50% AcOEt in hexane)
  5. customrecrystallized from AcOEt

Sources & evidence

ORD record
ord-2ca58f434a1548cb83a3e37fce4768f0
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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