Hydrochloric Acid → HCID 86743635, compound

HRID 329358Notes

Reaction equation

HRID 329358 reaction equation
[ClH:1].[Br-:2].[C:3]([O:6][C@@H:7]1[C@@H:24]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:23][C@@:22]2([CH3:31])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][C@H:15]([N+:38]3([CH3:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[C@H:16]2[O:32][C:33](=[O:37])[CH2:34][CH2:35][CH3:36])[CH2:8]1)(=[O:5])[CH3:4].C(OCC)C>ClCCl.CC(C)=O>[ClH:1].[Br-:2].[C:3]([O:6][C@@H:7]1[C@@H:24]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:23][C@@:22]2([CH3:31])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][C@H:15]([N+:38]3([CH3:44])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]3)[C@H:16]2[O:32][C:33](=[O:37])[CH2:34][CH2:35][CH3:36])[CH2:8]1)(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 1825543-(Acetyloxy)-17-(butanoyloxy)-16-(1-methylpiperidin-1-ium-1-yl)-2-(piperidin-1-yl)androstane bromide

Product 1

HCID 86743635HCID 86743635, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride gas Was passed through a solution of 1-[(2β, 3α, 5α, 16β, 17α)-3-(acetyloxy)-17-(1-oxobutoxy)-2-(1-piperidinyl)-androstan-16-yl]-1-methylpiperidinium bromide, (0.5 g) in dichloromethane (40 ml), then the solution was evaporated to give a froth. The product was dissolved in acetone and diethyl ether was added to precipitate an amorphous solid, Which Was filtered off and washed with ether. The solid was heated under reflux in acetone to give 1-[(2β, 3α, 5α, 16β, 17α)-3-(acetyloxy)-17-(1-oxobutoxy)-2-(1-piperidinyl)-androstan-16-yl]-1-methylpiperidinium bromide hydrochloride as prisms (0.45 g), m.p. 220°-228° C., [α]D20 =+57.2° (c 1.32 in CHCl3).

Workup

  1. customthe solution was evaporated
  2. customto give a froth
  3. customto precipitate an amorphous solid, Which
  4. filtrationWas filtered off
  5. washwashed with ether
  6. temperatureThe solid was heated
  7. temperatureunder reflux in acetone

Sources & evidence

ORD record
ord-b9ff280bc862488c8f97a0fb453d4e12
Source dataset
uspto-grants-1990_01
Patent number
US04891366

Reaction notes

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