Pyrrolidine → HCID 14762160, compound

HRID 1611426Notes

Reaction equation

HRID 1611426 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-99b8db0ff23f4f1f94dfa1dfe0509c36
Source dataset
uspto-grants-2006_01
Patent number
US06987188B2

Reaction notes

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