Hydrochloric Acid → HCID 17955463, compound

HRID 916553Notes

Reaction equation

HRID 916553 reaction equation
[ClH:1].[CH:2]1[C:14]2[CH:13]([CH2:15][CH2:16][N:17]([CH3:23])[CH2:18][CH2:19][C:20]([Cl:22])=[O:21])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[F:24][C:25]1[CH:26]=[C:27]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:28]=[CH:29][C:30]=1[F:31].C([O-])([O-])=O.[K+].[K+].Cl>CO.C(OCC)C.ClCCl>[ClH:22].[ClH:1].[F:24][C:25]1[CH:26]=[C:27]([N:32]2[CH2:37][CH2:36][N:35]([C:20](=[O:21])[CH2:19][CH2:18][N:17]([CH2:16][CH2:15][CH:13]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[C:6]4[C:14]3=[CH:2][CH:3]=[CH:4][CH:5]=4)[CH3:23])[CH2:34][CH2:33]2)[CH:28]=[CH:29][C:30]=1[F:31]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27831221-(3,4-Difluorophenyl)piperazineHCID 87822203HCID 87822203, compound

Product 1

HCID 17955463HCID 17955463, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-{[2-(9H-fluoren-9-yl)-ethyl]-methyl-amino}-propionic acid chloride hydrochloride (1.14 g), 4-(3,4-Difluoro-phenyl)-piperazine (587 mg), dichloromethane (25 ml) and 1 M aq. K2CO3 (25 ml) is stirred at room temperature for 1 hour. The phases are separated, the organic phase dried over sodium sulfate, filtered and evaporated. Purification by chromatography on silicagel (EtOAc/MeOH 7:3) afforded 1.2 g (100%) of a slightly colored oil. It is dissolved in 4 ml MeOH and acidified with 6 ml 1 M HCl in diethyl ether. More ether is added until the solution gets cloudy (ca. 3 ml). Crystallization at 5° afford 1.01 g (74%) of the desired product as dihydrochloride. M.p. 144°-154°. Anal: Calculated. for C29H33Cl2F2N3O.H2O: C, 61.48%; H, 6.22%; N, 7.41%. Found: C, 61.52%; H, 6.36%; N, 7.37%.

Workup

  1. customThe phases are separated
  2. dry with materialthe organic phase dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by chromatography on silicagel (EtOAc/MeOH 7:3)
  6. customafforded 1.2 g (100%) of a slightly colored oil
  7. customCrystallization at 5°

Sources & evidence

ORD record
ord-880a036b38c44e0b95fb96646dc21a3e
Source dataset
uspto-grants-2007_09
Patent number
US07271168B2

Reaction notes

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