Hydrochloric Acid → n-[2-(Diethylamino)ethyl]-n-(2-{[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]amino}ethyl)-3-[2-(1-naphthyl)ethoxy]propanamide dihydrochloride

HRID 556720Notes

Reaction equation

HRID 556720 reaction equation
[ClH:1].[CH2:2]([N:4]([CH2:41][CH3:42])[CH2:5][CH2:6][N:7]([CH2:25][CH2:26][NH:27][CH2:28][CH2:29][C:30]1[C:38]2[S:37][C:36](=[O:39])[NH:35][C:34]=2[C:33]([OH:40])=[CH:32][CH:31]=1)[C:8](=[O:24])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH3:3].C(OCC)C>CO>[ClH:1].[ClH:1].[CH2:41]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][N:7]([CH2:25][CH2:26][NH:27][CH2:28][CH2:29][C:30]1[C:38]2[S:37][C:36](=[O:39])[NH:35][C:34]=2[C:33]([OH:40])=[CH:32][CH:31]=1)[C:8](=[O:24])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH3:42]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 16035068Azd-3199

Product 1

HCID 66991768n-[2-(Diethylamino)ethyl]-n-(2-{[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]amino}ethyl)-3-[2-(1-naphthyl)ethoxy]propanamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 37 wt/wt % solution of hydrochloric acid (245.95 μL) was added to a solution of N-[2-(diethylamino)ethyl]-N-(2-{[2-(4-hydroxy-2-oxo-2,3-dihydro-1,3-benzothiazol-7-yl)ethyl]amino}ethyl)-3-[2-(1-naphthyl)ethoxy]propanamide (0.56 g) in methanol (5.6 mL) producing a clear solution that was stirred at room temperature for 15 mins. A 0.5 mL aliquot was taken from the bulk of the solution and treated with diethyl ether to form a mobile solid. This suspension was added back to the solution and the mixture was stirred at room temperature for 2 h. The title compound was then collected by filtration, washed with methanol (1.12 mL) and dried on the filter (0.46 g).

Workup

  1. customproducing a clear solution that
  2. customto form a mobile solid
  3. additionThis suspension was added back to the solution
  4. stirringthe mixture was stirred at room temperature for 2 h
  5. filtrationThe title compound was then collected by filtration
  6. washwashed with methanol (1.12 mL)
  7. customdried on the
  8. filtrationfilter (0.46 g)

Sources & evidence

ORD record
ord-12bc2406269944ea92cad507c823dd55
Source dataset
uspto-grants-2011_11
Patent number
US08058294B2

Reaction notes

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