Triethylamine → 2-[[4-[(Diphenylmethoxy)methyl]-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

HRID 565694Notes

Reaction equation

HRID 565694 reaction equation
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[C:17]1([CH:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:24][CH2:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>O>[C:17]1([CH:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:24][CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([CH2:2][C:3]3([CH3:16])[CH2:7][C:6]4[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=4[O:4]3)[CH2:28][CH2:27]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27624204-((Diphenylmethoxy)methyl)piperidineHCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

Product 1

HCID 221110022-[[4-[(Diphenylmethoxy)methyl]-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

In an autoclave, a mixture of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.5 g), 4-[(diphenylmethoxy)methyl]piperidine (3.0 g), and triethylamine (7.4 mL) was stirred under argon gas at 180° C. for 15 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1) to provide 2.4 g of 2-[[4-[(diphenylmethoxy)methyl]-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine. Yield 95%. This product was treated with 0.45 g of oxalic acid and, then, recrystallized from ethanol to provide 1.8 g of the title compound. Yield 58%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f022465e6a50441bb8d098226f383756
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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