Hydrochloric Acid → HCID 178436866, compound

HRID 1198654Notes

Reaction equation

HRID 1198654 reaction equation
[ClH:1].[Br:2][C:3]1[C:7]2[CH:8]=[C:9]([CH2:12][O:13][C:14]3[C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[N:17]=[C:16]([CH2:24][CH3:25])[CH:15]=3)[CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[N:33]=[N:34][N:35](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:36]=1>CO.C(O)C>[ClH:1].[Br:2][C:3]1[C:7]2[CH:8]=[C:9]([CH2:12][O:13][C:14]3[C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[N:17]=[C:16]([CH2:24][CH3:25])[CH:15]=3)[CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[NH:36][N:35]=[N:34][N:33]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 191027734-[(3-bromo-2-(2-(2-triphenylmethyl-2H-tetrazol-5-yl)phenyl)benzofuran-5-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline

Product 1

HCID 178436866HCID 178436866, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (1 ml) was added to a suspension of 4-[(3-bromo-2-(2-(2-triphenylmethyl-2H-tetrazol-5-yl)phenyl)benzofuran-5-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline (A) (650 mg) in methanol (2 ml) and ethanol (4 ml). The mixture was warmed gently until the solid dissolved and then left to stand for 2 hours. The precipitated solid was filtered off, slurried with ether (10 ml) and recrystallised from methanol to give 4-[(3-bromo-2-(2-(1H-tetrazol-5-yl)phenyl)benzofuran-5-yl)methoxy]-2-ethyl-5,6,7,8-tetrahydroquinoline hydrochloride, m.p. 210°-212° C.; NMR (d6 -DMSO): 1.3(t, 3H), 1.65-1.9(m, 4H), 2.5-2.7(m, 2H), 2.9-3.1(m, 4H), 5.6(s, 2H), 7.55(s, 1H), 7.6(s, 2H), 7.7(s, 1H), 7.75-7.85(m, 2H), 7.9-8.0(m, H); mass spectrum (+ve fast atom bombardment (+FAB), DMSO/Methanol/nitrobenzyl alcohol(NBA)): 532 (M+H)+ ; microanalysis, found: C, 57.0; H, 4.6; N, 12.4%; C27H24BrN5O2.HCl requires: C, 57.2; H, 4.45; N, 12.4%.

Workup

  1. temperatureThe mixture was warmed gently until the solid
  2. dissolutiondissolved
  3. waitleft
  4. filtrationThe precipitated solid was filtered off
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-28a10e7e262c45c19de5ef9d79baac0f
Source dataset
uspto-grants-1994_01
Patent number
US05281613

Reaction notes

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