1,3-Dibromopropane → 4-(3-Bromopropoxy)-2,2-dimethyl-1-(1-piperidinyl)indan

HRID 1253156Notes

Reaction equation

HRID 1253156 reaction equation
[OH-].[K+].[CH3:3][C:4]1([CH3:20])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[OH:13])[CH:5]1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[Br:21][CH2:22][CH2:23][CH2:24]Br>C(Cl)Cl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:21][CH2:22][CH2:23][CH2:24][O:13][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH2:12][C:4]([CH3:20])([CH3:3])[CH:5]2[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 20137132HCID 20137132, compound

Product 1

HCID 201371304-(3-Bromopropoxy)-2,2-dimethyl-1-(1-piperidinyl)indan

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Potassium hydroxide (1.44 g) is added to a stirred solution of the 4-hydroxy compound of Step 4 above (5 g) in methylene chloride (44 ml) and stirring is continued under N2 for 30 min. 1,3-Dibromopropane (20.7 ml) and tetrabutyl ammonium chloride (0.63 g) are added and the mixture is stirred at RT for about 70 hours. The reaction mixture is diluted with methylene chloride, washed with H2O, dried, filtered and the filtrate evaporated in vacuo. The residue is chromatographed (silica gel, hexane/ether) affording the purified desired product as an oil.

Workup

  1. stirringthe mixture is stirred at RT for about 70 hours
  2. washwashed with H2O
  3. customdried
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. customThe residue is chromatographed (silica gel, hexane/ether)
  7. customaffording the
  8. custompurified desired product as an oil

Sources & evidence

ORD record
ord-f40ec48196e243118f3792fae3390191
Source dataset
uspto-grants-1988_05
Patent number
US04748164

Reaction notes

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