4-Amino-1-methylpiperidine → HCID 9798459, compound

HRID 1285336Notes

Reaction equation

HRID 1285336 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]([C:13]([OH:15])=O)[C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]1=2.[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1>O1CCCC1>[CH3:27][N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:13]([CH:5]2[C:4]3[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=3[C:2](=[O:1])[NH:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]2=3)=[O:15])[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 23301798HCID 23301798, compound

Product 1

HCID 9798459HCID 9798459, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A quantity of 3.5 gm (0.022 mol) of N,N'-carbonyldiimidazole is added to a suspension of 5 gm (0.02 mol) of 5,11-dihydro-6-oxo-6H-dibenz[b,e]azepin-11-carboxylic acid in 100 ml of tetrahydrofuran, and the mixture is heated to 40° C. for 30 minutes. Then, 2.5 gm (0.022 mol) of 4-amino-1-methylpiperidine are added, and the mixture is heated for a further two hours at 40° C. After cooling, the solvent is removed in vacuo, and the residue is purified by column chromatography on silica gel [ethylene chloride/methanol (9:1)]. Subsequently, 4.8 gm (68%) of the desired compound, M.p.: 230°-231° C., are obtained from the eluate. According to the mixed melting point, thin layer chromatography, and IR spectrum, the substance is identical to the product obtained in Example 3.

Workup

  1. temperaturethe mixture is heated for a further two hours at 40° C
  2. temperatureAfter cooling
  3. customthe solvent is removed in vacuo
  4. customthe residue is purified by column chromatography on silica gel [ethylene chloride/methanol (9:1)]

Sources & evidence

ORD record
ord-13cb8797df504dba89138713dba6402d
Source dataset
uspto-grants-1986_01
Patent number
US04567178

Reaction notes

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