HCID 18184534, compound → HCID 18184532, compound

HRID 1358470Notes

Reaction equation

HRID 1358470 reaction equation
C(O)(=O)C(O)=O.C([O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:24]=1[NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)[NH:20][CH2:19][CH2:18]2)C1C=CC=CC=1>C(O)(=O)C.Cl>[ClH:37].[Cl:38][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][C:34]=1[Cl:37])[CH2:30][CH:21]1[C:22]2[C:17](=[CH:16][C:15]([OH:14])=[C:24]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:23]=2)[CH2:18][CH2:19][NH:20]1

Participants

4

Reactant 1

HCID 18184534HCID 18184534, compound

Product 1

HCID 18184532HCID 18184532, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-[6-benzyloxy-1-(3,4-dichloro-benzyl)-1,2,3,4-tetrahydro-isoquinolin-7-yl]-methanesulfonamide oxalate (0.5 g, 0.00085 mol) in 15 mL of acetic acid and 30 mL of conc. HCl was refluxed for 1 h, evaporated to dryness and the residue was crystallized from methanol-ether mixture. Yield 0.23 g (62%). mp 249-250° C. 1H NMR (Me2SO-d6) 300 MHz: δ 10.17 (s, 1H), 9.23 (brs, 2H), 8.84 (s, 1H), 7.75 (s, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.42 (d, J=8.1 Hz, 1H), 7.10 (s, 1H), 6.75 (s, 1H), 4.70 (brs, 1H), 3.28-3.43 (brs, 4H), 3.10-3.22 (m, 1H), 2.96-3.04 (m, 1H), 2.90 (s, 3H). MS (ESI): 402 (MH+).

Workup

  1. customevaporated to dryness
  2. customthe residue was crystallized from methanol-ether mixture

Sources & evidence

ORD record
ord-4115a39d5a574994951cc791db4fa452
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

Loading…