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Triethylamine → {1-[4-(4-Fluoro-phenyl)phthalazin-1-yl]piperidin-4-yl}-methyl-carbamic acid tert-butyl ester

HRID 1012960
Notes
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Reaction equation

HRID 1012960 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][N:3]=1.[C:19]([O:23][C:24](=[O:33])[N:25]([CH3:32])[CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C>CN(C=O)C.ClCCl>[C:19]([O:23][C:24](=[O:33])[N:25]([CH:26]1[CH2:27][CH2:28][N:29]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:4][N:3]=2)[CH2:30][CH2:31]1)[CH3:32])([CH3:22])([CH3:20])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21152391-Chloro-4-(4-fluorophenyl)phthalazineHCID 27568064-N-Boc-4-N-Methyl-aminopiperidine

Product 1

HCID 58157128{1-[4-(4-Fluoro-phenyl)phthalazin-1-yl]piperidin-4-yl}-methyl-carbamic acid tert-butyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 6228Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

Add 1-chloro-4-(4-fluorophenyl)-phthalazine (3.00 g, 11.6 mmol) to a solution of methyl-piperidin-4-yl-carbamic acid tert-butyl ester (2.98 g, 13.9 mmol) and triethylamine (3.52 g., 34.8 mmol) in DMF (30 mL). Heat at 130° C. for 3 days. Dissolve the reaction mixture in dichloromethane and wash with brine. Dry the organic phase with sodium sulfate, filter, and concentrate under reduced pressure. Purify the resulting residue by flash chromatography (20:5:1, hexane:ethyl acetate: 2 M ammonia in methanol) to yield the title compound as a solid (4.45 g, 88%). ES/MS m/z 437.2 (M+1).

Workup

  1. washwash with brine
  2. dry with materialDry the organic phase with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customPurify the resulting residue by flash chromatography (20:5:1, hexane:ethyl acetate: 2 M ammonia in methanol)

Sources & evidence

ORD record
ord-5c9f3cc8906441889ca44d7048524c4d
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981892B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes