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Tetrahydrofuran → Ammonium Hydroxide

HRID 1034145
Notes
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Reaction equation

HRID 1034145 reaction equation
Cl.[CH3:2][CH:3]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[CH3:4].[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C(N(CC)CC)C.C1COCC1>C(Cl)Cl>[NH4+:12].[OH-:5].[CH3:2][CH:3]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:26]=[CH:25][C:22]([CH2:23][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31268PyrrolidineHCID 19385508HCID 19385508, compound

Product 2

HCID 14923Ammonium HydroxideHCID 105246341-(2-Isopropoxy-phenyl)-4-(4-pyrrolidin-1-ylmethyl-benzyl)-piperazine

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]benzyl chloride hydrochloride (5.0 g, 0.012 mol), pyrrolidine (8.95 g, 0.126 mol), excess triethylamine, and THF (50 mL) was stirred at room temperature for 24 h. The reaction was then diluted with methylene chloride and washed with water. The organic layer was separated, dried (Na2SO4), filtered, and evaporated to a yellow oil. The residue was chromatographed on silica gel using 95:4.5:0.5/CHCl3:MeOH:NH4OH as eluant to give 1-[[4-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]phenyl]methyl]pyrrolidine as an oil, 5.00 g (100%). This material (4.95 g, 0.013 mol) was dissolved in i-PrOH (100 mL) and acidified with concentrated HCl to pH 3. The resulting solid was collected by filtration to give 1-[[4-[[1-[2-(1-methylethoxy)phenyl]-4-piperazinyl]methyl]phenyl]methyl]pyrrolidine dihydrochloride hydrate as a white powder, 4.83 g (80%), m.p. 270-280 (browning) 280°-300° C. 1H NMR and mass spectral analysis supported the assigned structure.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to a yellow oil
  6. customThe residue was chromatographed on silica gel using 95:4.5:0.5/CHCl3

Sources & evidence

ORD record
ord-84f121f2a91d4f8ea5825063f91339e6
Source dataset
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05314885

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes