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Water → 8-(3-Bromopropoxy)-4-piperidino-2,3-dihydrobenzopyran

HRID 3771
Notes
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Reaction equation

HRID 3771 reaction equation
[OH-].[K+].O.[OH:4][C:5]1[C:14]2[O:13][CH2:12][CH2:11][CH:10]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1.[Br:21][CH2:22][CH2:23][CH2:24]Br>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[Br:21][CH2:22][CH2:23][CH2:24][O:4][C:5]1[C:14]2[O:13][CH2:12][CH2:11][CH:10]([N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 212889988-Hydroxy-4-piperidino-2,3-dihydrobenzopyran

Product 1

HCID 212889948-(3-Bromopropoxy)-4-piperidino-2,3-dihydrobenzopyran

Reagents, catalysts & solvents 2

HCID 70681
Tetrabutylammonium Chloride
Catalyst
HCID 3283Diethyl EtherSolvent

Procedure

Crushed potassium hydroxide (4.1 g) and tetrabutyl ammonium chloride (2.2 g) and H2O (5 ml) are added to a stirred mixture of the product obtained in Step 3. (17.2 g) and 1,3-dibromopropane (74.8 ml). The reaction mixture is stirred under nitrogen overnight, diluted with diethyl ether, and extracted with 5% aq. HCl. The acidic solution is washed with ether, sat'd NaCl, dried, filtered and evaporated in vacuo yielding the desired product as an oil.

Workup

  1. extractionextracted with 5% aq. HCl
  2. washThe acidic solution is washed with ether
  3. customdried
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-11041e93a6764496b437ae0e8552152e
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04722925

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes