HCID 90410893, compound → HCID 90410895, compound

HRID 717379Notes

Reaction equation

HRID 717379 reaction equation
[Li].[AlH3].[CH2:3]([O:10][C:11]1[C:19](/[CH:20]=[CH:21]\[N+:22]([O-])=O)=[CH:18][CH:17]=[CH:16][C:12]=1[N:13]([CH3:15])[CH3:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>>[NH2:22][CH2:21][CH2:20][C:19]1[C:11]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[C:12]([CH:16]=[CH:17][CH:18]=1)[N:13]([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 90410893HCID 90410893, compoundHCID 131734159HCID 131734159, compound

Product 1

HCID 90410895HCID 90410895, compound

Conditions

Temperature
5 °C

Procedure

Into a 1000-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed oxolane (150 mL). This was followed by the addition of alumane lithium (5.6 g, 165.08 mmol, 3.35 equiv) in several batches at 0° C. To the mixture was added a solution of 2-(benzyloxy)-N,N-dimethyl-3-[(Z)-2-nitroethenyl]aniline (14.7 g, 49.27 mmol, 1.00 equiv) in tetrahtdrofuran (150 mL) dropwise with stirring at 0-10° C. The resulting solution was stirred overnight at 25° C. The mixture was cooled to 0-5° C. The reaction was then quenched by the addition of 6 mL of water, 18 mL of NaOH (10%) and 6 mL of water. The resulting solution was extracted with 2×500 mL of ethyl acetate and the organic layers combined. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (1:50-1:20). This resulted in 6.4 g (48%) of 3-(2-aminoethyl)-2-(benzyloxy)-N,N-dimethylaniline as light yellow oil. MS (ESI) m/z 271 ([M+H]+).

Workup

  1. customInto a 1000-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred overnight at 25° C
  4. temperatureThe mixture was cooled to 0-5° C
  5. customThe reaction was then quenched by the addition of 6 mL of water, 18 mL of NaOH (10%) and 6 mL of water
  6. extractionThe resulting solution was extracted with 2×500 mL of ethyl acetate
  7. dry with materialThe mixture was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThis resulted in 6.4 g (48%) of 3-(2-aminoethyl)-2-(benzyloxy)-N,N-dimethylaniline as light yellow oil

Sources & evidence

ORD record
ord-3ab48b9a13834675a6f23b09c5f6b80f
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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