HCID 12909379, compound → HCID 20310626, compound

HRID 1763653Notes

Reaction equation

HRID 1763653 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][CH2:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[C:6](=[O:15])[C:5]=12.[CH3:16][N:17]([CH3:23])[CH2:18][CH2:19][CH2:20][Mg]Cl>O1CCCC1>[OH:15][C:6]1([CH2:20][CH2:19][CH2:18][N:17]([CH3:23])[CH3:16])[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9][CH2:10][N:4]2[CH:3]=[CH:2][CH:1]=[C:5]12

Participants

4

Reactant 2

HCID 12909379HCID 12909379, compoundHCID 178483494HCID 178483494, compound

Product 1

HCID 20310626HCID 20310626, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 16 g., (0.081 mole) of 6,11-dihydro-5H-pyrrolo[2,1-b][3]benzazepin-11-one in 300 ml. tetrahydrofuran (THF) is added 150 ml. of 1.0N solution of 3-dimethylaminopropyl magnesium chloride in THF. After stirring for 40 minutes at ice-bath temperature and for 1.5 hours at 25° C., the bulk of the solvent is distilled below 45° C. under reduced pressure. The residue is dissolved in 500 ml. of methylene chloride and the Grignard adduct is hydrolyzed by the dropwise addition of 15 ml. water with cooling in an ice bath. The methylene chloride solution is decanted and the gelatinous precipitate is extracted three times with 80 ml. portions of boiling benzene. The combined organic extracts are washed with water and then evaporated under reduced pressure to yield, after crystallization from ethanol, 11-hydroxy-11-(3-dimethylaminopropyl)-6,11-dihydro-5H-pyrrolo-[2,1-b][3]benzazepine, m.p. 68°-70° C.

Workup

  1. waitfor 1.5 hours at 25° C.
  2. distillationthe bulk of the solvent is distilled below 45° C. under reduced pressure
  3. dissolutionThe residue is dissolved in 500 ml
  4. additionof methylene chloride and the Grignard adduct is hydrolyzed by the dropwise addition of 15 ml
  5. temperaturewater with cooling in an ice bath
  6. customThe methylene chloride solution is decanted
  7. extractionthe gelatinous precipitate is extracted three times with 80 ml
  8. washThe combined organic extracts are washed with water
  9. customevaporated under reduced pressure
  10. customto yield
  11. customafter crystallization from ethanol, 11-hydroxy-11-(3-dimethylaminopropyl)-6,11-dihydro-5H-pyrrolo-[2,1-b][3]benzazepine, m.p. 68°-70° C.

Sources & evidence

ORD record
ord-4de4d7327bc64097bb1f61fa452aece1
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

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