1-Pyrrolidineethanamine → HCID 18367611, compound

HRID 380024Notes

Reaction equation

HRID 380024 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][C:15]=1[CH3:23].[NH2:24][CH2:25][CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:24][CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:20])=[CH:16][C:15]=1[CH3:23]

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 821314-Bromo-3-methylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 18367611HCID 18367611, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (2.68 g) was added to a solution of 4-bromo-3-methyl benzoic acid (3.0 g), 1-(2-aminoethyl)pyrrolidine (1.78 ml) and 1-hydroxybenzotriazole hydrate (1.89 g) in dry N,N-dimethylformamide (30 ml). The reaction was stirred at room temperature for 24 hours. The solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with brine. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluting with dichloromethane:methanol (9:1) to give the sub-title compound as an oil. (3.55 g).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica gel eluting with dichloromethane:methanol (9:1)

Sources & evidence

ORD record
ord-c993661a761848a2862519adfd1368c6
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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