Hexane → 4-Amino-3,5-dichloro-alpha-[[[6-[2-[[2-(2-pyridinyl)ethyl]thio]ethoxy]hexyl]amino]methyl]benzenemethanol

HRID 2108141Notes

Reaction equation

HRID 2108141 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]([CH2:11][NH2:12])[OH:10])=[CH:4][C:3]=1[Cl:13].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][S:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.CCCCCC>CN(C=O)C>[NH2:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([CH:9]([CH2:11][NH:12][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][S:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[OH:10])=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8058HexaneHCID 217242Benzenemethanol, 4-amino-alpha-(aminomethyl)-3,5-dichloro-HCID 23045257HCID 23045257, compound

Product 1

HCID 230452724-Amino-3,5-dichloro-alpha-[[[6-[2-[[2-(2-pyridinyl)ethyl]thio]ethoxy]hexyl]amino]methyl]benzenemethanolYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-α-(aminomethyl)-3,5-dichlorobenzenemethanol (0.56 g,), 2-[2-[[2-[(6-bromohexyl)oxy]ethyl]thio]ethyl]pyridine (0.58 g,) and DEA (0.26 g,) in DMF (10 ml) was stirred under nitrogen for 2 h. The solvent was evaporated in vacuo and the residual oil partitioned between 8% sodium bicarbonate solution (100 ml) and dichloromethane (100 ml). The aqueous phase was re-extracted with dichloromethane (100 ml) and the combined organic phases dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System G (98:2:1) gave an oil. Trituration with hexane afforded the title compound (451 mg,) as a solid m.p. 59.5°-62°. T.l.c. (System E 40:10:1) Rf 0.32.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residual oil partitioned between 8% sodium bicarbonate solution (100 ml) and dichloromethane (100 ml)
  3. extractionThe aqueous phase was re-extracted with dichloromethane (100 ml)
  4. customthe combined organic phases dried
  5. customevaporated in vacuo
  6. customto give an oil
  7. customPurification by FCC
  8. washeluting with System G (98:2:1)
  9. customgave an oil

Sources & evidence

ORD record
ord-d10b901232dc4bed917a225c3c8c8998
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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