1-Pyrrolidineethanamine → 1-[[2-(Pyrrolidino)ethyl]amino]-7-methoxy-9H-xanthene-9-one

HRID 1719364Notes

Reaction equation

HRID 1719364 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[C:15]2[C:6]([O:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]2=[O:17])=[CH:5][CH:4]=1.[NH2:18][CH2:19][CH2:20][N:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[N:21]1([CH2:20][CH2:19][NH:18][C:12]2[C:13]3[C:14](=[O:17])[C:15]4[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:16]=4)[O:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 13441-PyrrolidineethanamineHCID 710342-Methoxyxanthone

Product 1

HCID 135047621-[[2-(Pyrrolidino)ethyl]amino]-7-methoxy-9H-xanthene-9-oneYield 80.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-chloro and 3-chloro isomers of 7-methoxyxanthone (32.6 g, 0.125 mole) of N-(2-aminoethyl)pyrrolidine (19.43 g, 0.17 mole) were refluxed in 150 mL of pyridine for 24 h with exclusion of moisture. The pyridine and excess of diamine was removed by vacuum distillation (ca. 12 mmHg, bath temp. 60°-72° C.), The distillation residue was dissolved in 200 mL of acetic acid, poured in 1.7 L water filtered and basified with NaOH pellets. The yellow-orange precipitate was filtered, washed with water an dried to give 34 g solid, which was chromatographed on silica gel. The first fraction was eluted with CHCl3. It was a mixture of starting chloroisomers and some minor by-products (18.5 g=56.7% melting range 135°-145° C. The desired compound was eluted with CHCl3 /EtOH (80:20) (13 g=30.7%), mp-93°-94° C. The analytical sample was recrystallized from ethanol, mp= 92°-93° C.

Workup

  1. customThe pyridine and excess of diamine was removed by vacuum distillation (ca. 12 mmHg, bath temp. 60°-72° C.)
  2. dissolutionThe distillation residue was dissolved in 200 mL of acetic acid
  3. additionpoured in 1.7 L water
  4. filtrationfiltered
  5. filtrationThe yellow-orange precipitate was filtered
  6. washwashed with water
  7. customan dried

Sources & evidence

ORD record
ord-c431065a74ba4159baec6ec5b3d23c48
Source dataset
uspto-grants-1985_09
Patent number
US04539412

Reaction notes

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