1-Bromopentane → HCID 131718536, compound

HRID 1728649Notes

Reaction equation

HRID 1728649 reaction equation
[ClH:1].[CH2:2]1[O:27][C:26]2[CH:25]=[CH:24][C:6]([O:7][CH2:8][C@H:9]3[C@H:14]([C:15]4[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=4)[CH2:13][CH2:12][NH:11][CH2:10]3)=[CH:5][C:4]=2[O:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>C(O)C>[ClH:1].[CH2:2]1[O:27][C:26]2[CH:25]=[CH:24][C:6]([O:7][CH2:8][C@H:9]3[C@H:14]([C:15]4[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=4)[CH2:13][CH2:12][N:11]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:10]3)=[CH:5][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 131718534HCID 131718534, compound

Product 1

HCID 131718536HCID 131718536, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound (6) (1 g) was dissolved in abs. ethanol (50 ml). K2CO3 (0.7 g) and 1-bromopentane (0.63 ml) were added. Reflux for 6 h, filtering and evaporation to dryness gave a crystalline mass which was extracted with NaOH(4N)ether. The etheral layer was dried, evaporated and purified on a silica gel column using CH2Cl2 /CH3OH 9/1 as eluent. Precipitated as the hydrochloride from acetone/ether. Yield 0.5 g. M.p. 57° C.

Workup

  1. temperatureReflux for 6 h
  2. filtrationfiltering
  3. customevaporation to dryness
  4. customgave a crystalline mass which
  5. extractionwas extracted with NaOH(4N)ether
  6. customThe etheral layer was dried
  7. customevaporated
  8. custompurified on a silica gel column
  9. customPrecipitated as the hydrochloride from acetone/ether

Sources & evidence

ORD record
ord-6ab3dc38cf5e403aa7bd1666554a9133
Source dataset
uspto-grants-1994_07
Patent number
US05328917

Reaction notes

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