Acetic Anhydride → HCID 14538666, compound

HRID 441955Notes

Reaction equation

HRID 441955 reaction equation
[OH:1][CH2:2][C:3]1([CH2:20][CH3:21])[CH:12]2[N:7]([CH2:8][CH2:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:11]=32)[CH2:6][CH2:5][CH2:4]1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:22]([O:1][CH2:2][C:3]1([CH2:20][CH3:21])[CH:12]2[N:7]([CH2:8][CH2:9][C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][C:11]=32)[CH2:6][CH2:5][CH2:4]1)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 658931-Hydroxymethyl-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine

Product 1

HCID 14538666HCID 14538666, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.50 g. (8.82 mmoles) of 1-hydroxymethyl-1-ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine are dissolved in 15 ml. of absolute pyridine. 15 ml. of acetic anhydride are added to the solution, and the mixture is allowed to stand at room temperature for three days. Thereafter the solution is evaporated in vacuo, and the oily residue is stirred with a 5% sodium hydrocarbonate solution. The separated solid substance is filtered off, washed with water, dried, and recrystallized first from aqueous methanol and then from methanol. 1.75 g. (61.2%) of the title compound are obtained in the form of shiny crystals melting at 96°-97° C.

Workup

  1. customThereafter the solution is evaporated in vacuo
  2. filtrationThe separated solid substance is filtered off
  3. washwashed with water
  4. customdried
  5. customrecrystallized first from aqueous methanol

Sources & evidence

ORD record
ord-e7ce94b906b249a0a1f7d9061f7b2647
Source dataset
uspto-grants-1977_08
Patent number
US04044012

Reaction notes

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