Ethyl Bromide → HCID 21122005, compound

HRID 543649Notes

Reaction equation

HRID 543649 reaction equation
[Br:1][CH2:2]C.[C:4]([O:7][C@H:8]1[C@@H:13]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:12][C@H:11]2[C@H:20]3[C@H:30]([CH2:31][CH2:32][C@:9]12[CH3:10])[C@:28]1([CH3:29])[C@H:23]([CH2:24][CH2:25][C@@H:26]([N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:27]1)[CH2:22][CH2:21]3)(=[O:6])[CH3:5]>ClCCl.C(OCC)C>[Br-:1].[C:4]([O:7][C@H:8]1[C@@H:13]([N+:14]2([CH3:2])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH2:12][C@H:11]2[C@H:20]3[C@H:30]([CH2:31][CH2:32][C@:9]12[CH3:10])[C@:28]1([CH3:29])[C@H:23]([CH2:24][CH2:25][C@@H:26]([N:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:27]1)[CH2:22][CH2:21]3)(=[O:6])[CH3:5]

Participants

5

Reactant 2

HCID 6332Ethyl BromideHCID 22826492HCID 22826492, compound

Product 1

HCID 21122005HCID 21122005, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Bromoethane (1.5 g) was added to a solution of 2β,16β-di-(1-piperidinyl)-5α-androstan-17β-ol acetate (1.0 g) in a mixture of dry dichloromethane (10 ml) and dry diethyl ether (10 ml). The solution was sealed in a pressure bottle and set aside at room temperature for 7.5 h. The solvent was then removed under reduced pressure, without heating, to afford a white solid, which was dissolved in the minimum of dry dichloromethane (8.0 ml) and dry diethyl ether (30 ml) was added to precipitate the crude product (0.3 g). The material from the mother liquor was retreated with bromomethane (1.05 g) in dry dichloromethane (7.0 ml) and dry diethyl ether (7.0 ml), as above, to yield a further quantity (0.3 g) of crude product. The procedure was repeated once again to obtain a final amount (0.25 g) of crude product. The three crops were combined and crystallised from dichloromethaneacetone to afford 1-[17β-acetyloxy-2β-(1-piperidinyl)-5α-androstan-16β-yl]-1-methyl-piperidinium bromide (0.30 g), m.p. 213°-219° C.; [α]D -19.5° (c 0.36 in CHCl3).

Workup

  1. customThe solution was sealed in a pressure bottle
  2. customThe solvent was then removed under reduced pressure
  3. temperaturewithout heating
  4. customto afford a white solid, which
  5. additionwas added
  6. customto precipitate the crude product (0.3 g)
  7. customas above, to yield a further quantity (0.3 g) of crude product
  8. customto obtain a final amount (0.25 g) of crude product
  9. customcrystallised from dichloromethaneacetone

Sources & evidence

ORD record
ord-e8e3645acc014a17a8bb1180b02fe70f
Source dataset
uspto-grants-1984_05
Patent number
US04447425

Reaction notes

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