Hydrochloric Acid → HCID 22266081, compound

HRID 489620Notes

Reaction equation

HRID 489620 reaction equation
CC(OC(=O)[N:7]([C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]([N:23]2[CH2:28][CH2:27][CH:26]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][N:36](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[CH:30]=3)[CH2:25][CH2:24]2)=[O:22])[CH:20]=1)[CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)(C)C.[ClH:52].C(O)(C)C.CCOCC>CO>[ClH:52].[ClH:52].[ClH:52].[ClH:52].[NH2:36][CH2:35][C:31]1[CH:30]=[C:29]([CH:26]2[CH2:27][CH2:28][N:23]([C:21]([C:19]3[CH:18]=[N:17][CH:16]=[C:15]([NH:7][CH2:8][C:9]4[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=4)[CH:20]=3)=[O:22])[CH2:24][CH2:25]2)[CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3776IsopropanolHCID 69030745HCID 69030745, compound

Product 1

HCID 22266081HCID 22266081, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{5-[1-(4-{3-[N,N-Bis-(tert-butoxycarbonyl)amino-methyl]-phenyl}-piperidin-1-yl)-methanoyl]-pyridin-3-yl}-pyridin-3-ylmethyl-carbamic acid dimethyl-ethyl ester (0.0250 g, 0.0356 mmol) was treated with 5-6 M HCl in isopropanol (1.0 mL, 8.0 mmol) and stirred at ambient temperature. After 90 minutes the reaction mixture was diluted with methyl alcohol (0.5 mL) and stirring was continued for an additional 75 minutes. Dripping the reaction solution into ether (40 mL) with vigorous stirring afforded a white precipitate which was collected by filtration, washed with fresh ether (3.0 mL), and dried to afford 1-[4-(3-aminomethyl-phenyl)-piperidin-1-yl]-1-{5-[(pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-methanone tetrahydrochloride (0.0160 g): 1H NMR (300 MHz, DMSO-d6) δ 8.60-8.95 (m, 2H), 8.39 (br s, 2H), 8.29 (d, J=8.0 Hz, 1H), 7.97-8.25 (m, 2H), 7.65-7.85 (m, 2H), 7.47 (d, J=8.0 Hz, 2H), 7.20-7.38 (m, 3H), 4.63 (s, 2H), 4.43-4.61 (m partially obscured, 1H), 4.00 (AB q, J=5.8 Hz, 2H), 3.05-3.25 (m partially obscured, 1H), 2.72-2.95 (m, 2H), 1.80-1.88 (m, 1H), 1.47-1.77 (m, 3H); MS (CI) m/z 402 (M+H).

Workup

  1. stirringstirring
  2. customafforded a white precipitate which
  3. filtrationwas collected by filtration
  4. washwashed with fresh ether (3.0 mL)
  5. customdried

Sources & evidence

ORD record
ord-bd7f4a261d764ba8a15f0b6d60d9f0d4
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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