HCID 56989982, compound → HCID 86742269, compound

HRID 845495Notes

Reaction equation

HRID 845495 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][C@@H:8]2C[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C@H:7]12)[CH3:2].CC(NN(CC)NC(C)C)C>>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][C@@H:8]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C@H:7]12)[CH3:2]

Participants

3

Reactant 2

HCID 56989982HCID 56989982, compoundHCID 86742270HCID 86742270, compound

Product 1

HCID 86742269HCID 86742269, compound

Procedure

A solution of 5-n-butyloctahydro-2-oxo-1H-indoleacetic acid ethyl ester (3aα, 7aα) (VI) (5.0 g, 0.0178 mole) in N,N-bis-(1-methylethyl)aminoethylamine (4.49 g, 0.0267 mole) is heated at 100° C. for 18 hours. The solution is concentrated at reduced pressure to an oil. The oil is dissolved in 2-propanol and the solution is treated with a saturated solution of hydrogen chloride in 2-propanol. The solution is diluted with anhydrous diethyl ether and allowed to crystallize. The crystals are filtered. Recrystalliztion from acetonitrile-diethyl ether yields pure 5-n-butyloctahydro-2-oxo-1H-indoleacetamide N-[bis[1-methylethyl]amino]ethyl]·hydrochloride (3aα, 7aα) (VII) with mp 116°-118° C.

Workup

  1. concentrationThe solution is concentrated at reduced pressure to an oil
  2. dissolutionThe oil is dissolved in 2-propanol
  3. additionthe solution is treated with a saturated solution of hydrogen chloride in 2-propanol
  4. additionThe solution is diluted with anhydrous diethyl ether
  5. customto crystallize
  6. filtrationThe crystals are filtered

Sources & evidence

ORD record
ord-cd973947d5ae494c95e5dd2aa2a51a8c
Source dataset
uspto-grants-1988_07
Patent number
US04758585

Reaction notes

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