Diethyl Ether → HCID 14371619, compound

HRID 1464005Notes

Reaction equation

HRID 1464005 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C@H:11]2[NH2:19])[CH:6]=[CH:7][C:8]=1[Cl:9].C(OC(OCC)CBr)C.C(=O)([O-])[O-].[K+].[K+].CCOCC>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH:11]2[NH2:19])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 14371620HCID 14371620, compound

Product 1

HCID 14371619HCID 14371619, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1.0 grams(3.65 mmol) of Compound L from step B, 0.55 mL (3.65 mmol) 2-bromoacetaldehyde diethyl acetal, and 1.0 grams (7.3 mmol) anhydrous potassium carbonate in 35 mL dry DMF was stirred at 150° C. for 4 hours. After cooling to room temperature, the mixture was poured into 300 mL ether, washed with three 50 mL portions of water, dried (MgSO4) and evaporated. The residue was purified by flash chromatography, eluting with 1:1 hexane-ethyl acetate to give 1.1 grams (77%) of N-(2,2-diethoxyethyl)-trans-1-(3-methoxy-4-chlorophenyl-2-indanamine (Compound M) as an oil, 200 MHz NMR(CDCl3) d 1.15(tr,6H,J=7 Hz), 2.70-290(m,3H), 3.20-3.70(m,6H), 4.09(d,1H,J=8 Hz), 4.55(tr,1H,J=5 Hz), 6.70-6.90(m,3H), 7.10-7.30(m,4H).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with three 50 mL portions of water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 1:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-1408ff0ff5024cd08ae3e001e631f764
Source dataset
uspto-grants-1994_04
Patent number
US05302716

Reaction notes

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