Hydrochloric Acid → HCID 23627265, compound

HRID 1423102Notes

Reaction equation

HRID 1423102 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:10][C@@H:9]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])=O)(C)(C)C.Cl>O1CCOCC1>[CH:23]1([O:22][C:16]2[CH:15]=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][C@@H:9]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[CH3:35])[CH2:10]3)[CH:19]=[CH:18][C:17]=2[O:20][CH3:21])[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66825123HCID 66825123, compound

Product 1

HCID 23627265HCID 23627265, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of intermediate (S)-4-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-(2-methyl-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (215 mg, 0.447 mmol) in 1,4-dioxane (2 mL) was then treated with a 4 N solution of hydrogen chloride (4 mL) and stirred for 2 h. The reaction was then evaporated to a colorless solid, suspended in EtOAc (10 mL), and washed with a saturated aqueous K2CO3 solution (3 mL) followed by brine (3 mL). The organic portion was then dried over MgSO4, filtered, and evaporated to afford the title compound as a burgundy colored oil (127 mg, 75%). 1H NMR (CDCl3) 7.26-7.11 (m, 4H), 6.78 (d, J=8.8, 1H), 6.53 (d, J=2.9, 1H), 6.43 (dd, 8.7, 2.6, 1H), 4.74-4.71 (m, 1H), 3.78 (s, 3H), 3.39-3.35 (m, 2H), 3.16-3.08 (m, 2H), 2.96 (td, J=11.2, 2.9, 1H), 2.87-2.70 (m, 2H), 2.56-2.49 (m, 1H), 2.36 (s, 3H), 1.92-1.72 (m, 6H), 1.61-1.57 (m, 2H). 13C NMR 148.4, 146.5, 144.8, 136.7, 136.4, 130.7 (CH), 130.2 (CH), 126.8 (CH), 126.1 (CH), 113.3 (CH), 108.6 (CH), 106.8 (CH), 80.6, (CH), 56.8 (CH2), 56.8 (CH3), 55.3 (CH), 51.3 (CH2), 46.0 (CH2), 37.9 (CH2), 32.97 (CH2), 24.2 (CH2), 19.8 (CH3). LC/MS (Method A) 5.03 min, [M+1]+ 381.

Workup

  1. customThe reaction was then evaporated to a colorless solid
  2. washwashed with a saturated aqueous K2CO3 solution (3 mL)
  3. dry with materialThe organic portion was then dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-31d929d6d88847f5ba90d49b605e8aeb
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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