Hydrochloric Acid → (+/-)-N-isobutyl-N-(2,3,4,5-tetrahydro-1-benzoxepin-8-ylmethyl)morpholine-2-carboxamide hydrochloride

HRID 2264169Notes

Reaction equation

HRID 2264169 reaction equation
[CH2:1]([N:5]([CH2:21][C:22]1[CH:32]=[CH:31][C:25]2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:24]=2[CH:23]=1)[C:6]([CH:8]1[O:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3].[ClH:33]>O1CCOCC1>[ClH:33].[CH2:1]([N:5]([CH2:21][C:22]1[CH:32]=[CH:31][C:25]2[CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:24]=2[CH:23]=1)[C:6]([CH:8]1[O:13][CH2:12][CH2:11][NH:10][CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60209725HCID 60209725, compound

Product 1

HCID 60209726(+/-)-N-isobutyl-N-(2,3,4,5-tetrahydro-1-benzoxepin-8-ylmethyl)morpholine-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 0.798 g (1.79 mmol) of (±)-tert-butyl 2-{[isobutyl(2,3,4,5-tetrahydro-1-benzoxepin-8-ylmethyl)amino]carbonyl}morpholine-4-carboxylate in 3.6 mL of dioxane cooled in an ice-bath was added 3.6 mL (14.4 mmol, 8 equiv) of 4M HCl in dioxane. The solution was stirred 30 minutes with cooling, then for 3.5 hours at ambient temperature. The solution was concentrated under reduced pressure, the residue triturated with ether, and dried under vacuum to give the product as a white solid. MS (m+1)=347.3; H NMR (400 MHz, CD3OD) 7.12 (m, 1H), 6.84 (m, 2H), 4.8-4.6 (m, 2H), 4.58-4.39 (m, 1H), 4.1-3.85 (m, 4H), 3.5-3.35 (m, 3H), 3.24 (m, 2H), 3.15-2.92 (m, 1H), 2.78 (m, 2H), 2.02 (m, 1H), 1.95 (m, 2H), 1.71 (m, 2H), 0.89 (m, 6H).

Workup

  1. temperaturewith cooling
  2. waitfor 3.5 hours at ambient temperature
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe residue triturated with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3d33b541611243158d50bb77c7698d2e
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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