Hydrochloric Acid → HCID 67923918, compound

HRID 981996Notes

Reaction equation

HRID 981996 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:26])[CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[N:24]=[CH:23][C:22]([F:25])=[CH:21][N:20]=3)[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.CCN(CC)CC.[F:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([Cl:41])=[O:40])=[CH:37][CH:36]=1.Cl.CCO>C(Cl)Cl>[ClH:41].[F:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([O:26][CH:9]([C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)[CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[N:20]=[CH:21][C:22]([F:25])=[CH:23][N:24]=3)[CH2:15][CH2:14]2)=[O:40])=[CH:37][CH:36]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 30865141-(4-Fluorophenyl)-4-[4-(5-fluoropyrimidin-2-yl)piperazin-1-yl]butan-1-ol--hydrogen chloride (1/1)

Product 1

HCID 67923918HCID 67923918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A cold (5° C.) mixture of 1-(4-fluorophenyl)-4-(4-(5-fluoro-2-pyrimidinyl)-1-piperazinyl)-1-butanol monohydrochloride. (3.0 g, 7.8 mmol) and Et3N (2.40 mL, 17.2 mmol) in CH2Cl2 (55 mL) was treated dropwise (10 min) with 4-fluorobenzoyl chloride (1.11 mL, 9.4 mmol). The cooling bath was removed and the reaction mixture stirred at 23° C. for 20 h before being diluted with CH2Cl2 (250 mL). The organic solution was washed with water (30 mL), saturated Na2CO3 solution to bring pH to 9, water (30 mL) and brine, dried (MgSO4) and concentrated in vacuo to a crude mixture which was purified on silica gel column using a mixture of 20-30% AcOEt in CH2Cl2. The appropriate fractions were concentrated in vacuo to a thick syrup, 3.4 g, 93%. The free base was solubilized in EtOH and treated with HCl in EtOH (one equivalent). The solvent was removed under reduced pressure leaving a gum which was crystallized from AcOEt affording analytical sample mp 94°-8° C.

Workup

  1. customThe cooling bath was removed
  2. additionbefore being diluted with CH2Cl2 (250 mL)
  3. washThe organic solution was washed with water (30 mL), saturated Na2CO3 solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo to a crude mixture which
  6. customwas purified on silica gel column
  7. additiona mixture of 20-30% AcOEt in CH2Cl2
  8. concentrationThe appropriate fractions were concentrated in vacuo to a thick syrup, 3.4 g, 93%
  9. customThe solvent was removed under reduced pressure
  10. customleaving a gum which
  11. customwas crystallized from AcOEt affording analytical sample mp 94°-8° C.

Sources & evidence

ORD record
ord-f6fac5855fca4c1f8ee298f0db03d624
Source dataset
uspto-grants-1991_02
Patent number
US04994460

Reaction notes

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