Hydrochloric Acid → HCID 67996164, compound

HRID 659643Notes

Reaction equation

HRID 659643 reaction equation
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][C:15]([CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH:22]([NH:26]C(=O)OC(C)(C)C)[CH2:21]3)=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2.[ClH:35]>O1CCOCC1>[ClH:35].[ClH:35].[CH3:34][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][C:15]([CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH:22]([NH2:26])[CH2:21]3)=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67996554HCID 67996554, compound

Product 1

HCID 67996164HCID 67996164, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 50-mL round-bottom flask was charged with tert-butyl 1-((9-(3-(dimethylamino)propyl)-9H-carbazol-3-yl)methyl)piperidin-3-ylcarbamate (200 mg, 0.43 mmol, 1.00 equiv) and conc. HCl (1 mL) in 1,4-dioxane (3 mL). The resulting mixture was stirred at room temperature for 1 hour. Upon completion, the resulting mixture was concentrated on a rotary evaporator to give the crude that was re-crystallized from 1:1 CH3OH/ether affording 1-((9-(3-(dimethylamino)propyl)-9H-carbazol-3-yl)methyl)piperidin-3-amine dihydrochloride yellow solid (0.2 g, 98%). LCMS: [M+H]+: 365. 1H NMR (D2O, 300 MHz) δ 8.08-8.05 (m, 2H), 7.53-7.44 (m, 4H), 7.28-7.23 (m, 1H), 4.47 (br, 2H), 4.31 (t, 2H), 3.73 (br, 1H), 3.55-3.47 (m, 2H), 3.06-2.90 (m, 4H), 2.64 (s, 6H), 2.22-2.13 (m, 3H), 2.05-2.00 (m, 1H), 1.67-1.54 (m, 2H).

Workup

  1. concentrationUpon completion, the resulting mixture was concentrated on a rotary evaporator
  2. customto give the crude that
  3. customwas re-crystallized from 1:1 CH3OH/ether

Sources & evidence

ORD record
ord-17c52a92f3584b15a3f729d01ecb0bfd
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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