Bromine → HCID 20374951, compound

HRID 1448993

Reaction equation

HRID 1448993 reaction equation
[Na].[CH2:2]([O:9][C:10]1[CH2:14][CH:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.BrBr.[CH3:25][NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(O)CCCCCC.C1C=CC=CC=1>[CH2:27]([N:26]([CH3:25])[CH:12]1[CH:11]([O:9][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:10]([O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:14][CH:13]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 24408BromineHCID 93190N-MethylheptylamineHCID 5360545SodiumHCID 20374931HCID 20374931, compound

Product 1

HCID 20374951HCID 20374951, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8129HeptanolSolvent

Procedure

0.23 g of sodium are dissolved in 30 ml of 1-heptanol at 50° under nitrogen. Dropwise, with stirring, there is added 4.88 g of N-heptyl-N-methyl-2-bromo-4,5-bibenzyloxycyclopentane-1-amine (obtainable from 3,5-dibenzyloxy-2-cyclopentene by the addition of bromine and reaction with 1-equivalent of methyl heptylamine), dissolved in 30 ml of benzene. Stirring is carried on for 6 hours at 50°. After cooling, 100 ml of benzene is added thereto. This is washed with water. The organic phase is dried over MgSO4 and the solvent is distilled off. After chromatographic purification of the residue (silica gel/chloroform:acetone=9:1), N-heptyl-N-methyl-5-heptyloxy-2,4-dibenzyloxy-cyclopentane-1-amine is obtained.

Workup

  1. stirringStirring
  2. customis carried on for 6 hours at 50°
  3. temperatureAfter cooling
  4. washThis is washed with water
  5. dry with materialThe organic phase is dried over MgSO4
  6. distillationthe solvent is distilled off
  7. customAfter chromatographic purification of the residue (silica gel/chloroform:acetone=9:1)

Sources & evidence

ORD record
ord-94ef12ff946346dc905bfdf4177f9e32
Source dataset
uspto-grants-1980_02
Patent number
US04188403

Linked notes

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