Hydrochloric Acid → HCID 86600328, compound

HRID 1987416Notes

Reaction equation

HRID 1987416 reaction equation
[ClH:1].Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13](C(C3(O)CCCCC3)CN3CCN(C)CC3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.Br[C:33]1[CH:38]=[CH:37][C:36]([CH:39](C2(O)CCCCC2)[CH2:40][N:41]2[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]2)=[CH:35][CH:34]=1.FC1C=CC(B(O)[OH:63])=CC=1.FC1C=CC(C2C=CC(C(C3(O)CCCCC3)CN3CCN(C)CC3)=CC=2)=CC=1.Cl>C(OCC)C.O1CCOCC1>[ClH:1].[ClH:1].[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:37]3([OH:63])[CH2:38][CH2:33][CH2:34][CH2:35][CH:36]3[CH2:39][CH2:40][N:41]3[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]3)=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 2856454-Fluorophenylboronic acidHCID 11383918HCID 11383918, compoundHCID 68852885HCID 68852885, compoundHCID 68855247HCID 68855247, compound

Product 1

HCID 86600328HCID 86600328, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

In an analogous manner to Example 135, step 3, 1-[1-(4′-fluoro-1,1′-biphenyl-4-yl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexanol dihydrochloride was prepared from 1-[1-(4-bromophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclohexanol using 4-fluorophenylboronic acid. Salt formation: A solution of 1-[1-(4′-fluoro-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′-fluoro-1,1′-biphenyl-4-yl)-2-(4-methylpiperazin-1-ylethyl]cyclohexanol dihydrochloride. MS (ESI) m/z 397 ([M+H]+); HRMS: calcd for C25H33FN2O.2.00 HCl, 468.2110. found (ESI), 397.2639.

Workup

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

Sources & evidence

ORD record
ord-f487c1842182434b8a261d974ad5c0d1
Source dataset
uspto-grants-2009_06
Patent number
US07550485B2

Reaction notes

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