Diisopropylethylamine → Ethyl 1-({[2-(5-chloro-1H-indol-3-yl)ethyl]amino}carbonyl)cyclobutanecarboxylate

HRID 1700362Notes

Reaction equation

HRID 1700362 reaction equation
Cl.[Cl:2][C:3]1[CH:14]=[C:13]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[C:15]1([C:24]([O-])=[O:25])([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>ClCCl>[Cl:2][C:3]1[CH:14]=[C:13]2[C:6](=[CH:5][CH:4]=1)[NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH:12][C:24]([C:15]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]1)=[O:25]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 18317994Monoethyl 1,1-cyclobutanedicarboxylate

Product 1

HCID 11163887Ethyl 1-({[2-(5-chloro-1H-indol-3-yl)ethyl]amino}carbonyl)cyclobutanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

23.1 g of 5-chlorotryptamine hydrochloride, 17.3 g of monoethyl cyclobutanedicarboxylate, 36 ml of diisopropylethylamine and 33.7 g of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate are stirred for 20 hours at ambient temperature in 200 ml of dichloromethane. After washing with water, drying over sodium sulphate and filtering off the organic phase over Celite, evaporation under reduced pressure enables the expected product to be isolated.

Workup

  1. washAfter washing with water
  2. dry with materialdrying over sodium sulphate
  3. filtrationfiltering off the organic phase
  4. customover Celite, evaporation under reduced pressure
  5. customto be isolated

Sources & evidence

ORD record
ord-ab50d7e3732f4d9f96748499779790a2
Source dataset
uspto-grants-2002_02
Patent number
US06350757B1

Reaction notes

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