Hydrochloric Acid → HCID 67307869, compound

HRID 445206Notes

Reaction equation

HRID 445206 reaction equation
C(S[C:4]1[S:8][C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]=2[O:21][C:22]2[CH:36]=[CH:35][C:25]([O:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:24][CH:23]=2)=[CH:6][CH:5]=1)C.O1CC[CH2:39][CH2:38]1.[S:42]([OH:46])([O-])(=O)=[O:43].S(O)(OO)(=O)=O.[K+].[ClH:54]>O.ClCCl.CO>[ClH:54].[CH2:38]([S:42]([C:4]1[S:8][C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]=2[O:21][C:22]2[CH:23]=[CH:24][C:25]([O:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)=[CH:35][CH:36]=2)=[CH:6][CH:5]=1)(=[O:46])=[O:43])[CH3:39]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 58338602HCID 58338602, compoundHCID 131730192HCID 131730192, compound

Product 1

HCID 67307869HCID 67307869, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add 1-(2-(4-(2-(5-(ethylthio)thiophen-2-yl)-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine (226 mg, 0.43 mmol), tetrahydrofuran (8.7 mL) and methanol (8.7 mL) to a round bottom flask under nitrogen. Cool the resulting solution to 0° C. and add a solution of potassium peroxymonosulfate sulfate (535 mg. 0.87 mmol) in water (4.5 mL). Stir the resulting mixture at 0° C. for 30 min. Allow the mixture to warm to room temperature and stir for 1 hour. Load the mixture onto an SCX acidic ion exchange column. Flush column with a 1:1 mixture of methanol and dichloromethane then elute with a 1:1 mixture of 2M ammonia in methanol and dichloromethane. Concentrate the ammonia containing eluent in vacuo to give an off white foam. Dissolve the foam in dichloromethane and treat with HCl (1M in ether; 900 uL). Concentrate the resulting mixture in vacuo to obtain the title compound (142 mg, 0.24 mmol): mass spectrum (m/z): 552 (M+1-HCl).

Workup

  1. temperatureAllow the mixture to warm to room temperature
  2. stirringstir for 1 hour
  3. customFlush column
  4. additionwith a 1:1 mixture of methanol and dichloromethane
  5. washthen elute with a 1:1 mixture of 2M ammonia in methanol and dichloromethane
  6. concentrationConcentrate the ammonia containing eluent in vacuo
  7. customto give an off white foam
  8. concentrationConcentrate the resulting mixture in vacuo

Sources & evidence

ORD record
ord-157e690a3420449fa0510b70877302e3
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

Loading…