Hydrochloric Acid → HCID 22397016, compound

HRID 1370366Notes

Reaction equation

HRID 1370366 reaction equation
C(=[N:14][C:15]1[C:16]2[C:17]3[CH2:28][CH2:27][N:26]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:25][CH2:24][C:18]=3[NH:19][C:20]=2[CH:21]=[CH:22][CH:23]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl>O1CCCC1>[CH2:29]([N:26]1[CH2:27][CH2:28][C:17]2[C:16]3[C:15]([NH2:14])=[CH:23][CH:22]=[CH:21][C:20]=3[NH:19][C:18]=2[CH2:24][CH2:25]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22396680HCID 22396680, compound

Product 1

HCID 22397016HCID 22397016, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzhydrylidene-(3-benzyl-1,2,3,4,5,6-hexahydro-azepino[4,5-b]indol-10-yl)amine (0.794 g, 1.74 mmol) in tetrahydrofuran was added 1 M hydrochloric acid (10.0 mL). The mixture was stirred at room temperature for 10 min, and then tetrahydrofuran was removed in vacuo. The aqueous mixture was extracted with ethyl acetate (2×). The acidic residue was basified with ammonia and extracted with dichloromethane (3×). The combined dichloromethane solution was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness to give 0.416 g (82%) of the title compound: mp 164-165° C.; 1H NMR (300 MHz, CDCl3) δ 7.76, 7.45-7.26, 6.88, 6.74, 6.29, 3.86, 3.27-3.23, 3.06-2.97; MS (ESI+) m/z 292 (M++H).

Workup

  1. customtetrahydrofuran was removed in vacuo
  2. extractionThe aqueous mixture was extracted with ethyl acetate (2×)
  3. extractionextracted with dichloromethane (3×)
  4. dry with materialThe combined dichloromethane solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-a8eec254054046b397a52e1dfb69ad27
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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