Hydrochloric Acid → HCID 19841180, compound

HRID 1638803Notes

Reaction equation

HRID 1638803 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([OH:15])=O)=[CH:8][C:7]=2[CH:16]=1.[ClH:19].Cl.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:33]=[C:34]([O:38][CH3:39])[C:35]=1[O:36][CH3:37])[CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.P(C#N)(=O)(OCC)OCC.Cl>C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[ClH:19].[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[CH2:12][CH2:11][CH2:10][C:9]([C:13]([N:30]3[CH2:29][CH2:28][N:27]([CH2:26][C:25]4[CH:33]=[C:34]([O:38][CH3:39])[C:35]([O:36][CH3:37])=[C:23]([O:22][CH3:21])[CH:24]=4)[CH2:32][CH2:31]3)=[O:15])=[CH:8][C:7]=2[CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 76257Diethyl cyanophosphonateHCID 10106052HCID 10106052, compoundHCID 128285011-[(3,4,5-Trimethoxyphenyl)methyl]piperazine;dihydrochloride

Product 1

HCID 19841180HCID 19841180, compoundYield 27.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Using 2,3-dimethoxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (2 g), 1-(3,4,5-trimethoxybenzyl)piperazine dihydrochloride (3.5 g), N,N-dimethylformamide (30 ml), triethylamine (3.3 g) and diethyl phosphorocyanidate (2.5 ml), a reaction as that described in Example 6 is carried out. The product is purified by silica gel column chromatography (hexane:acetone=1:1) to give an oily product which is converted to the hydrochloride in ethyl acetate to yield 1-(2,3-dimethoxy-6,7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3,4,5-trimethoxybenzyl)piperazine hydrochloride (1.2 g) as colorless crystals, m.p. 138°-142° C.

Workup

  1. customa reaction as
  2. customThe product is purified by silica gel column chromatography (hexane:acetone=1:1)
  3. customto give an oily product which

Sources & evidence

ORD record
ord-5738d7cc0dd6438aae278cd6b2cea450
Source dataset
uspto-grants-1989_11
Patent number
US04880809

Reaction notes

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