Acetic Acid → HCID 22390432, compound

HRID 1071931Notes

Reaction equation

HRID 1071931 reaction equation
[I-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]#[C:11][CH2:12][N:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:7]=[CH:6][C:5]=1[C:20]1(O)[CH:27]2[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:29][CH:21]1[CH2:22]3)[CH2:26]2.Cl[Si](C)(C)C.C(O)(=O)C>C(#N)C.ClCCl.[Zn]>[ClH:3].[CH:27]12[CH2:26][CH:25]3[CH2:24][CH:23]([CH2:22][CH:21]([CH2:29]3)[CH:20]1[C:5]1[CH:6]=[CH:7][C:8]([C:10]#[C:11][CH2:12][N:13]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:9][C:4]=1[Cl:3])[CH2:28]2

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 22390462HCID 22390462, compound

Product 1

HCID 22390432HCID 22390432, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

3.46 g of sodium iodide are added, under an inert atmosphere, to 3.68 g of 2-{2-chloro-4-[3-(1-azepanyl)prop-1-ynyl]phenyl}adamantan-2-ol (compound I′.1) in 20 ml of acetonitrile and 10 ml of dichloromethane, followed by 2.35 ml of chlorotrimethylsilane. The reaction mixture is stirred for 2 hours at 30° C., and then 1.06 ml of acetic acid are added, followed by 10 ml of acetonitrile and then 1.81 g of powdered zinc. The reaction mixture is heated at 80° C. for 3 hours, allowed to cool to room temperature, filtered and washed with diethyl ether. The organic phases are dried over sodium sulphate, and then the solvents are evaporated off under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with an 87.5/12.5 (v/v) cyclohexane/ethyl acetate mixture; m.p.=218° C. (HCl).

Workup

  1. temperatureThe reaction mixture is heated at 80° C. for 3 hours
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. washwashed with diethyl ether
  5. dry with materialThe organic phases are dried over sodium sulphate
  6. customthe solvents are evaporated off under reduced pressure
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica gel
  9. washeluting with an 87.5/12.5 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-429a3d44601a4f10904e906ee27b4d82
Source dataset
uspto-grants-2005_06
Patent number
US06908914B1

Reaction notes

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