Hydrochloric Acid → HCID 70129330, compound

HRID 343570Notes

Reaction equation

HRID 343570 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]([N:37]5[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]5)=[O:36])=[CH:29][CH:28]=4)[CH2:20][CH2:19][C:18]4(OCC[O:21]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:28]=[CH:29][C:30]([O:33][CH2:34][C:35]([N:37]5[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]5)=[O:36])=[CH:31][CH:32]=4)[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 700813064-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(2-[4-(1-piperidinocarbonylmethoxy)phenyl]ethynyl)cyclohexane

Product 1

HCID 70129330HCID 70129330, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(2-[4-(1-piperidinocarbonylmethoxy)phenyl]ethynyl)cyclohexane (0.232 g, 0.40 mmol) in tetrahydrofuran (9 mL) was treated with 3N hydrochloric acid (0.90 mL) as described in Example 12 above. The crude product was purified by chromatography (silica, 50% ethyl acetate/hexanes) and the solvent removed in vacuo to afford the titled compound as a resin (0.127 g, 59%). Anal. (C28H30O5.1/10 H2O) calcd: C 75.01, H 6.79, found: C 74.97, H 6.87. 1H-NMR (400 MHz, CDCl3) δ 7.41 (d, J=9.1 Hz, 2H), 7.22 (d, J=2.3 Hz, 1H), 7.11 (d-d, J=8.4 Hz, J=2.3 Hz, 1H), 6.92 (d, J=8.6, 1H), 6.86 (d, J=8.5, 1H),4.80 (p, 1H), 4.70 (s, 2H), 4.00 (s, 4H), 3.85 (s, 3H), 3.56 (t, J=5.5 Hz, 2H), 3.48 (t, J=5.5 Hz, 2H), 3.03 (d-t, J=6.1 Hz, J=14.3, 2H), 2.47 (d,br, J=14.9, 2H), 2.4-2.2 (m, 4H), 2.0 to 1.5 (m, 25H with H2O).

Workup

  1. customThe crude product was purified by chromatography (silica, 50% ethyl acetate/hexanes)
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7e1aede95d9c47779d1ab3acb1ccb89e
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

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