Formic Acid → HCID 90412034, compound

HRID 717380Notes

Reaction equation

HRID 717380 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:5]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:6]([CH:10]=[CH:11][CH:12]=1)[N:7]([CH3:9])[CH3:8].[CH:21](O)=O>>[CH2:14]([O:13][C:5]1[C:6]([N:7]([CH3:8])[CH3:9])=[CH:10][CH:11]=[C:12]2[C:4]=1[CH2:3][CH2:2][NH:1][CH2:21]2)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 90410895HCID 90410895, compound

Product 1

HCID 90412034HCID 90412034, compound

Conditions

Temperature
55 °C

Procedure

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-(2-aminoethyl)-2-(benzyloxy)-N,N-dimethylaniline (1 g, 3.70 mmol, 1.00 equiv), formic acid (10 mL) and (CHOH)n (89 mg). The resulting solution was stirred overnight at 55° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 10 mL of water. The pH value of the solution was adjusted to 10 with sodium hydroxide (10 mol/L). The resulting solution was extracted with 1×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×20 mL of water. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 1 g (96%) of 5-(benzyloxy)-N,N-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-amine as brown oil. MS (ESI) m/z 283 ([M+H]+).

Workup

  1. customInto a 100-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. additionThe resulting solution was diluted with 10 mL of water
  5. extractionThe resulting solution was extracted with 1×50 mL of ethyl acetate
  6. washThe resulting mixture was washed with 2×20 mL of water
  7. dry with materialThe mixture was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customThis resulted in 1 g (96%) of 5-(benzyloxy)-N,N-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-amine as brown oil

Sources & evidence

ORD record
ord-ad9f7c91578747379d478e61ce298aa3
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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