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Triethylamine → HCID 16755443, compound

HRID 346703
Notes
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Reaction equation

HRID 346703 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([C:13]([O-])=[O:14])[N:10]=[C:9]2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.[Li+].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:36]2[CH:37]=[CH:38][CH:39]=C[C:35]=2[N:34]=[N:33]1.NN1CCCCC1.C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([C:13]([NH:33][N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:14])[N:10]=[C:9]2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 166581-AminopiperidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23704465HCID 23704465, compound

Product 1

HCID 16755443HCID 16755443, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Part B: A mixture of the crude lithium 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-4,5-dihydro-1H-imidazole-4-carboxylate (1.0 gram, ˜0.0027 mol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophos-phate (BOP) (1.2 gram, 0.0027 mol), 1-aminopiperidine (0.3 gram, 0.003 mol) and triethylamine (1 ml) in DMF (30 ml) is stirred at room temperature for 16 hours. After concentration in vacuo, water is added and the resulting mixture is extracted (2×) with dichloromethane. The dichloromethane layers are collected, dried over MgSO4, filtered and concentrated in vacuo to give a residue that is further purified by flash chromatography (silicagel, dichloromethane/methanol=95/5 (v/v)) to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)—N—(piperidin-1-yl)-4,5-dihydro-1H-imidazole-4-carboxamide (380 mg, 31% yield). Melting point: 113–116° C. 1H-NMR (200 MHz, CDCl3): δ 1.33–1.48 (m, 2H), 1.60–1.80 (m, 4H), 2.68–2.82 (m, 4H), 4.28–4.35 (m, 2H), 4.84 (dd, J=11 and 9 Hz, 1H), 6.65 (br d, J=8 Hz, 2H), 7.11 (br d, J=8 Hz, 2H), 7.23–7.33 (m, 2H), 7.41 (d, J=2 Hz, 1H), 7.57 (br s, 1H).

Workup

  1. concentrationAfter concentration in vacuo, water
  2. additionis added
  3. extractionthe resulting mixture is extracted (2×) with dichloromethane
  4. customThe dichloromethane layers are collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue that
  9. customis further purified by flash chromatography (silicagel, dichloromethane/methanol=95/5 (v/v))

Sources & evidence

ORD record
ord-5825b019245e4157aa6d7ffe3def3c26
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07173044B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes