Hydrochloric Acid → HCID 22396559, compound

HRID 2306945Notes

Reaction equation

HRID 2306945 reaction equation
[CH3:1][N:2]([CH3:27])[C:3](=[O:26])[CH2:4][N:5]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]2[CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18][C:6]1=2.C(C(O)=O)(F)(F)F.[ClH:35]>C(Cl)Cl.CCOC(C)=O.CCOCC>[ClH:35].[CH3:1][N:2]([CH3:27])[C:3](=[O:26])[CH2:4][N:5]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18][C:6]1=2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 22396713HCID 22396713, compound

Product 1

HCID 22396559HCID 22396559, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 6-[2-(dimethylamino)-2-oxoethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.113 g, 0.305 mmol) was dissolved in CH2Cl2 (3 mL) at rt. CF3CO2H (1 mL) was added and the reaction mixture was stirred for 40 min. The reaction mixture was concentrated to give a crude product (0.145 g). The crude product was dissolved in EtOAc (3 mL), then 1 N HCl in Et2O (6 mL) was added and the precipitated salt was collected by filtration. N,N-Dimethyl-2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)acetamide hydrochloride (0.0896 g) was obtained in 95% yield. 1H NMR (300 MHz, CD3OD) δ 2.99, 3.14-3.17, 3.21-3.24, 3.26, 3.47-3.50, 5.16, 7.08, 7.15, 7.30, 7.50; MS (ESI+) for C16H21N3O m/z 272.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give a crude product (0.145 g)
  3. filtrationthe precipitated salt was collected by filtration

Sources & evidence

ORD record
ord-714057b1989744ee842c333ea842b768
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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