Pyrrolidine → HCID 14762160, compound

HRID 1760187Notes

Reaction equation

HRID 1760187 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7][CH2:6]2.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 755826-Methoxy-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 14762160HCID 14762160, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-methoxy-3,4-dihydro-1H-naphthalen-2-one (1) (5.64 g, 32 mmol) in methanol (60 mL) was treated with pyrrolidine (3.5 mL, 41.6 mmol) and the resultant mixture was stirred at ambient temperature for 1.5 h. The product precipitated from solution within minutes of the addition of pyrrolidine. The resultant suspension was cooled in an ice bath and the enamine product (2) was collected by filtration as a white solid (5.6 g, 76%). NMR (CDCl3): δ 1.86-1.94 (m, 4 H), 2.46 (t, 2H), 2.80 (t, 2 H), 3.19-3.25 (m, 4 H), 3.77 (s, 3 H), 5.10 (s, 1 H), 6.59-6.65 (m, 2 H) and 6.78 d, 1 H).

Workup

  1. customThe product precipitated from solution within minutes of the addition of pyrrolidine
  2. temperatureThe resultant suspension was cooled in an ice bath
  3. filtrationthe enamine product (2) was collected by filtration as a white solid (5.6 g, 76%)

Sources & evidence

ORD record
ord-dae01326074749c2a8ab960c4bcacfc1
Source dataset
uspto-grants-2005_01
Patent number
US06841552B1

Reaction notes

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