Triethylamine → HCID 53809650, compound

HRID 965213Notes

Reaction equation

HRID 965213 reaction equation
[CH2:1]([C:8]1[CH:25]=[CH:24][CH:23]=[CH:22][C:9]=1[NH:10][C@@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C@H:12]1[NH:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>C(OCC)C>[CH2:1]([C:8]1[CH:25]=[CH:24][CH:23]=[CH:22][C:9]=1[NH:10][C@@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C@H:12]1[N:20]([CH3:21])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 9840404HCID 9840404, compound

Product 1

HCID 53809650HCID 53809650, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (±) trans 1-(2-benzylanilino)-2-methylaminoindane (Example 2)(0.66 g, 2.0 mmol) in dry diethyl ether (25 ml) was treated with triethylamine (0.55 ml, 4.0 mmol) and ethyl chloroformate (0.21 ml, 2.2 mmol). After stirring at room temperature for 1 h, the reaction was concentrated in vacuo and the residue was partitioned between chloroform (25 ml) and water (25 ml). The organic layer was washed with water (3×25 ml) followed by brine (25 ml), and then concentrated in vacuo to give a brown oil (0.73 g) which crystallised on cooling and was used in the next stage without purification.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customthe residue was partitioned between chloroform (25 ml) and water (25 ml)
  3. washThe organic layer was washed with water (3×25 ml)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09ae88b0b7b34a4fb086a8592a94a365
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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