Triethylamine → HCID 15870089, compound

HRID 1584168Notes

Reaction equation

HRID 1584168 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][C:9](=[C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH:16]=[CH:15][C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]2=3)[CH2:8][CH2:7]1.[C:27]([O:31][C:32]([N:34]1[CH2:42][CH2:41][CH:37]([C:38](O)=[O:39])[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>>[C:27]([O:31][C:32]([N:34]1[CH2:42][CH2:41][CH:37]([C:38]([NH:3][CH2:4][CH2:5][N:6]2[CH2:11][CH2:10][C:9](=[C:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[CH:16]=[CH:15][C:14]4[CH:23]=[CH:24][CH:25]=[CH:26][C:13]3=4)[CH2:8][CH2:7]2)=[O:39])[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18431524HCID 18431524, compound

Product 1

HCID 15870089HCID 15870089, compound

Procedure

1-(2-Aminoethyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene) piperidine dihydrochloride (2.3 g, 6.0 mmol), 1-t-butoxycarbonylisonipecotic acid (1.6 g, 7.2 mmol), triethylamine (3.0 ml, 21.6 mmol) and 1-ethyl-3-(3-dimethlaminopropyl) carbodiimide hydrochloride (1.4 g, 7.2 mmol) were mixed, and the mixture was stirred at room temperature overnight. After evaporating the solvent, the residue was dissolved in 100 ml of dichloromethane, washed with 100 ml of 1 N hydrochloric acid, 100 ml of a 1 N aqueous, sodium hydroxide solution, and 50 ml of a saturated aqueous sodium chloride solution. The solvent was evaporated and the residue was purified by silica gel chromatography to obtain the titled compound.

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in 100 ml of dichloromethane
  3. washwashed with 100 ml of 1 N hydrochloric acid, 100 ml of a 1 N aqueous
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-655d9b8f40ae4101800c4e08b7b07a40
Source dataset
uspto-grants-1999_08
Patent number
US05932593

Reaction notes

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