1,1'-Carbonyldiimidazole → HCID 18621500, compound

HRID 324562Notes

Reaction equation

HRID 324562 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[NH2:22])[O:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1.C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1>C1(C)C=CC=CC=1>[O:29]=[C:28]1[N:22]=[C:21]2[CH:20]=[CH:19][C:4]([O:5][CH2:6][CH2:7][CH2:8][N:9]3[CH2:18][CH2:17][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH2:10]3)=[CH:3][C:2]2=[N:1]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 54549658HCID 54549658, compound

Product 1

HCID 18621500HCID 18621500, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N-[(3,4-diaminophenoxy)propyl]-1,2,3,4-tetrahydroisoquinoline (200 mg, 0.67 mmol) and CDI (162 mg, 1.0 mmol) in toluene (15 mL) was refluxed for 16 h, then evaporated. The residual solid was washed with EtOAc (2×5 mL) and CHCl3 (5 mL), then dried to give 107 mg (48%) of the title compound as a yellow powder. 1H NMR (DMSO-d6): 1.90-1.96 (m, 2H), 2.591 (d, 2H, J=7), 2.662 (t, 2H, J=5), 2.803 (t, 2H, J=5), 3.560 (s, 2H), 3.967 (t, 2H, J=6), 6.50-6.52 (m, 2H), 6.76-6.80 (m, 1H), 7.05-7.10 (m, 4H), 10.359 (s, 1H), 10.483 (s, 1H). The hydrochloride, mp. 210-5° C. (dec). Analysis, Calcd. for (C19H22ClN3O2+0.3 HCl): C, 61.55, H, 6.06, N, 11.33; Found: C, 61.57, H, 6.14, N, 11.05.

Workup

  1. temperaturewas refluxed for 16 h
  2. customevaporated
  3. washThe residual solid was washed with EtOAc (2×5 mL) and CHCl3 (5 mL)
  4. customdried

Sources & evidence

ORD record
ord-b5f0656e6701409fb215870210c16d47
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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