Diisopropylaniline → HCID 66795703, compound

HRID 1944816Notes

Reaction equation

HRID 1944816 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[CH:25]([C:28]1[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([CH3:37])[CH3:36])[C:29]=1[NH2:30])([CH3:27])[CH3:26]>C(O)C>[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]=[N:30][C:29]2[C:31]([CH:35]([CH3:36])[CH3:37])=[CH:32][CH:33]=[CH:34][C:28]=2[CH:25]([CH3:27])[CH3:26])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 32484DiisopropylanilineHCID 86663391HCID 86663391, compound

Product 1

HCID 66795703HCID 66795703, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.80 g (15.0 mmol) of 6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde and 2.70 g (15.0 mmol) of 2,6-diisopropylaniline in 50 ml of dry ethanol was refluxed overnight. The resulting mixture was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.). Yield 5.50 g (76%) of orange oil which crystallized at room temperature. Anal. calc. for C33H39N3: C, 82.97; H, 8.23; N, 8.80. Found: C, 83.10; H, 8.41; N, 8.68. 1H NMR (CDCl3): 8.41 (m, 1H, 3-H in Py), 8.38 (s, 1H, CH═N), 8.00 (m, 1H, 4-H in Py), 7.91 (d, J=8.6 Hz, 4-H in naphthyl), 7.88 (m, 1H, 8-H in naphthyl), 7.66 (d, J=8.6 Hz, 3-H in naphthyl), 7.56 (m, 1H, 5-H in Py), 7.37-7.47 (m, 3H, 5,6,7-H in naphthyl), 7.10-7.18 (m, 3H, 3,4,5-H in Ph), 3.60 (m, 2H, CH2N), 3.02 (sept, J=6.8 Hz, 2H, CHMe2), 1.18 (d, J=6.8 Hz, 6H, CHMeMe′), 1.19 (d, J=6.8 Hz, 6H, CHMeMe′), 0.95 (s, 9H, tBu).

Workup

  1. temperaturewas refluxed overnight
  2. customThe resulting mixture was evaporated to dryness
  3. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.)
  4. customYield 5.50 g (76%) of orange oil which crystallized at room temperature

Sources & evidence

ORD record
ord-cd6cc0a6b7ca4743aff7d214f986dc51
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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