Triethylamine → HCID 88182119, compound

HRID 2298243Notes

Reaction equation

HRID 2298243 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:20][CH2:19][N:11]2[C:12]3[C:17]([CH:18]=[C:10]2[CH2:9]1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C1COCC1>[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:20][CH2:19][N:11]2[C:12]3[C:17]([C:18]([C:23]([Cl:22])=[O:25])=[C:10]2[CH2:9]1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 15063418HCID 15063418, compound

Product 1

HCID 88182119HCID 88182119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (6,7,8,9-tetrahydro-pyrido[1,2-a]indol-8-yl)-carbamic acid tert-butyl ester (400 mg, 1.40 mmol) in dry THF (5 mL) was cooled to 0° C. Triphosgene (208 mg, 0.7 mmol) dissolved in dry THF (3 mL) and triethylamine (194 μL, 1.40 mmole) were added. A precipitation was formed. The reaction was allowed to reach room temperature and after 2 h the mixture was evaporated and the crude product was used in the next step. APCI-MS m/z: 345 [MH+] (analysis performed on a sample quenched with methanol, thus the mass corresponds to the methylester).

Workup

  1. customA precipitation
  2. customwas formed
  3. customthe mixture was evaporated
  4. customquenched with methanol

Sources & evidence

ORD record
ord-2e2084e90af24342bef80724fb3c06c9
Source dataset
uspto-grants-2002_12
Patent number
US06492406B1

Reaction notes

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