Hydrochloric Acid → HCID 86742776, compound

HRID 1382929Notes

Reaction equation

HRID 1382929 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([CH:12]([CH3:14])[CH3:13])[C@:7]([CH2:16][CH2:17][N:18]([CH3:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[N:28]([CH3:29])[C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=3[N:25]=1)([OH:15])[CH2:6][CH2:5]2.[C:35]1([N:41]=[C:42]=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[ClH:44]>C1(C)C=CC=CC=1.C(Cl)Cl.CCOCC.C(C(CCCC)C([O-])=O)C.[Sn+2].C(C(CCCC)C([O-])=O)C>[ClH:44].[ClH:44].[C:42](=[O:43])([O:15][C@:7]1([CH2:16][CH2:17][N:18]([CH3:34])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]2[N:28]([CH3:29])[C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=3[N:25]=2)[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[C@@H:8]1[CH:12]([CH3:14])[CH3:13])[NH:41][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 57028628HCID 57028628, compound

Product 1

HCID 86742776HCID 86742776, compoundYield 65%

Reagents, catalysts & solvents 4

HCID 93182-ethylhexanoic acid tin(II) saltCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2.32 g (0.005 mol) of [1S,2S]-6-fluoro-1,2,3,4-tetrahydro-1-isopropyl-2-[2-[methyl-[5-(1-methyl-2-benzimidazolyl)pentyl]amino]ethyl]-2-naphthalenol and 0.6 g (0 005 mol) of phenyl isocyanate in 5 ml of toluene is treated with 7.5 mg of tin(II) 2-ethylhexanoate and heated to 100° for 15 hours. After concentration under reduced pressure the oily residue is chromatographed on 160 g of silica gel with methanol/methylene chloride (3:2) as the elution agent. The oily product obtained is dissolved in methylene chloride and treated with an excess of hydrogen chloride in ether. There are obtained 2.15 g (65%) of [1S,2S]-6-fluoro-1,2,3,4-tetrahydro-1-isopropyl-2-[2-[methyl-[5-(1-methyl-2-benzimidazolyl)pentyl]amino]ethyl]-2-naphthyl carbanilate dihydrochloride, m.p. 157°-160°, as a colourless crystalline powder.

Workup

  1. temperatureheated to 100° for 15 hours
  2. concentrationAfter concentration under reduced pressure the oily residue
  3. customis chromatographed on 160 g of silica gel with methanol/methylene chloride (3:2) as the elution agent
  4. customThe oily product obtained

Sources & evidence

ORD record
ord-8796bd0f351341ddabf2a00c15fecfa0
Source dataset
uspto-grants-1989_02
Patent number
US04808605

Reaction notes

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