Hydrochloric Acid → HCID 131710748, compound

HRID 2380576Notes

Reaction equation

HRID 2380576 reaction equation
[ClH:1].Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][C:20]([OH:22])=O)[CH2:13][CH2:12]1.C(N(CC)CC)C.[NH:36]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=[CH:37]1.Cl>ClCCl.C(OC)(=O)C>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH:18]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:19][C:20]([N:36]2[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[O:22])[CH2:15][CH2:16]1.[OH2:4].[ClH:1].[ClH:1].[ClH:1].[ClH:1]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 64514761H-AzepineHCID 70187121HCID 70187121, compound

Product 2

HCID 9803033HCID 9803033, compoundHCID 131710748HCID 131710748, compoundYield 563.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6584Methyl AcetateSolvent

Procedure

1,1-Carbonydiimidazole (0.80 g, 4.9 mmol) was added to a solution of 4-[4-(2-methoxyphenyl)piperazin-1-yl]-3-phenylbutanoic acid dihydrochloride (2.00 g, 4.68 mmol) and triethylamine (0.95 g, 9.4 mmol) in dichloromethane (20 ml). After the cessation of gas evolution, a solution of azepine (0.51 g, 5.2 mmol) in dichloromethane (7 ml) was added and stirring continued overnight. The reaction mixture was concentrated under reduced pressure and the crude product chromatographed on silica gel, eluting with ethyl acetate: hexane (5:1) to afford an oil. The oil was dissolved in methyl acetate and acidified with ethereal hydrogen chloride to afford the title compound dihydrochloride hemihydrate as a colourless powder (1.08 g), m.p. 201.5-202.2 (dec.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude product chromatographed on silica gel
  3. washeluting with ethyl acetate: hexane (5:1)
  4. customto afford an oil

Sources & evidence

ORD record
ord-722ee7a643a94b7080b200194997dec0
Source dataset
uspto-grants-1994_11
Patent number
US05369103

Reaction notes

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