1-Hydroxybenzotriazole → HCID 18456238, compound

HRID 1272036Notes

Reaction equation

HRID 1272036 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH:37]1([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[CH2:41][CH2:40][CH2:39][CH2:38]1>CN(C=O)C.C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:7])[CH2:8][CH2:9][C:10]([N:45]2[CH2:46][CH2:47][N:42]([CH:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[CH2:43][CH2:44]2)=[O:12])=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 776043-(4-Chlorobenzoyl)propionic acidHCID 8064211-CyclopentylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18456238HCID 18456238, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(4-chlorobenzoyl)propionic acid (31.9 g, 150 mmol), DMF (200 ml), and N-hydroxybenzotriazole (40.6 g, 301 mmol) was added a solution of N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (28.8 g, 150 mmol) in DMF (100 ml). The mixture was stirred at room temperature for 1.5 hour, and a solution of 1-cyclopentylpiperazine (23.2 g, 150 mmol) in DCM (100 ml) was added. The mixture was stirred at room temperature for 4 hours, concentrated under reduced pressure, and the residue was distributed between ethyl acetate (1.0 I) and a saturated, aqueous NaHCO3 solution (1.0 I). Phases were separated, the organic layer was dried (MgSO4), and concentrated, and the residue was redissolved in 1 molar aqueous hydrochloric acid (150 ml). The solution was concentrated, and the residue was dried by coevaporation with ethanol. Recrystallization of the residue from ethanol yielded 31.1 g (54%) of the title compound. Concentration of the mother liquor gave additional 19.4 g (34%) of product.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. customPhases were separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. dissolutionthe residue was redissolved in 1 molar aqueous hydrochloric acid (150 ml)
  7. concentrationThe solution was concentrated
  8. dry with materialthe residue was dried by coevaporation with ethanol
  9. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-f187e24269924684be0f28c1fe4a8b12
Source dataset
uspto-grants-2007_04
Patent number
US07208497B2

Reaction notes

Loading…