N,N-Dimethyl-1,3-propanediamine → 4-amino-N-[3-(dimethylamino)propyl]-3-methoxybenzamide

HRID 1676518Notes

Reaction equation

HRID 1676518 reaction equation
N1(O[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([O:19][CH3:20])[CH:13]=2)C2C=CC=CC=2N=N1.[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26][NH2:27].C(N(CC)CC)C>O1CCCC1>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:27][CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:22])=[O:21])=[CH:13][C:14]=1[O:19][CH3:20]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8471TriethylamineHCID 106606854-Amino-3-methoxy-benzoic acid benzotriazol-1-yl ester

Product 1

HCID 580150584-amino-N-[3-(dimethylamino)propyl]-3-methoxybenzamideYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1.1371 g (4.0 mmole) of 4-amino-3-methoxy-benzoic acid benzotriazol-1-yl ester and 8 mL of dry tetrahydrofuran at 0 degrees was added 0.6131 g (6.0 mmole) of 3-dimethylamino-propylamine followed by 1.0119 g (10 mmole) of triethylamine. The cooling bath was removed and the mixture stirred at room temperature for 65 minutes. Volatiles were removed under reduced pressure and the residue taken up in ethyl acetate, and the organic layer washed twice with 50 mL of 0.5 M sodium carbonate, 50 mL water, and then 50 mL brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.8587 g 4-amino-N-(3-dimethylamino-propyl)-3-methoxy-benzamide, which was used without further purification.

Workup

  1. customThe cooling bath was removed
  2. customVolatiles were removed under reduced pressure
  3. washthe organic layer washed twice with 50 mL of 0.5 M sodium carbonate, 50 mL water
  4. dry with material50 mL brine, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9df11458c5f84c538434e8ddd9a937b9
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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