Hydrochloric Acid → HCID 68855817, compound

HRID 1986996Notes

Reaction equation

HRID 1986996 reaction equation
[ClH:1].Cl.CC1C=CC(C2C=CC(C3(O)CCCCC3CCN3CCN(C)CC3)=CC=2)=CC=1.C1(O)CCCCC1.C1(C)C=CC(B(O)O)=CC=1.[CH3:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][C:59]([CH:62]([C:71]3([OH:77])[CH2:76][CH2:75][CH2:74][CH2:73][CH2:72]3)[CH2:63][N:64]3[CH2:69][CH2:68][N:67]([CH3:70])[CH2:66][CH2:65]3)=[CH:58][CH:57]=2)=[CH:52][CH:51]=1.Cl>C(OCC)C.O1CCOCC1>[ClH:1].[ClH:1].[CH3:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:57]=[CH:58][C:59]([CH:62]([C:71]3([OH:77])[CH2:76][CH2:75][CH2:74][CH2:73][CH2:72]3)[CH2:63][N:64]3[CH2:69][CH2:68][N:67]([CH3:70])[CH2:66][CH2:65]3)=[CH:60][CH:61]=2)=[CH:52][CH:51]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7966CyclohexanolHCID 79799Tolylboronic acidHCID 11234753HCID 11234753, compoundHCID 86621020HCID 86621020, compound

Product 1

HCID 68855817HCID 68855817, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

In an analogous manner to Example 135, step 3, 1-[1-(4′-methyl-1,1′-biphenyl-4-yl)-2-(4-methylpiperazin-1-yl)ethylcyclohexanol dihydrochloride was prepared from 1-(4-bromophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexanol (see Example 180, step 3) using 4-tolylboronic acid. Salt formation: A solution of 1-[1-(4′-methyl-1,1′-biphenyl-4-yl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexanol, in diethyl ether (2 mL) was treated with a 4 N solution of hydrogen chloride in dioxane (1 mL) and stored in the refrigerator for 16 h. The resulting crystals were collected, washed with diethyl ether, and dried in vacuo to yield 1-[1-(4′-methyl-1,1′-biphenyl-4-yl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexanol dihydrochloride. MS (ESI) m/z 393 ([M+H]+); HRMS: calcd for C26H36N2O.2.00 HCl, 464.2361; found (ESI), 393.2913.

Workup

  1. customThe resulting crystals were collected
  2. washwashed with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a5711f9409cf43d595fc6bba6e2aba9d
Source dataset
uspto-grants-2009_06
Patent number
US07550456B2

Reaction notes

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