Hydrochloric Acid → 1-(4-Morpholinecarbonyl)-1,4-diazepane hydrochloride

HRID 2228480Notes

Reaction equation

HRID 2228480 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23]>ClCCl.CO>[ClH:23].[N:17]1([C:15]([N:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)=[O:16])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 155382851-(t-Butyloxycarbonyl)-4-(4-morpholinecarbonyl)-1,4-diazepane

Product 1

HCID 227070621-(4-Morpholinecarbonyl)-1,4-diazepane hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 1-(t-butyloxycarbonyl)-4-(4-morpholinecarbonyl)-1,4-diazepane (140.0 g, 0.44 mol) in dichloromethane:methanol (1:1, v/v, 600 ml) at 0° C. was saturated with hydrogen chloride gas and the reaction mixture was stirred at room temperature under nitrogen for 18 hours after which time the reaction mixture was evaporated under reduced pressure and slurried in ethyl acetate to give, after filtration, a white hygroscopic solid. This was further purified by slurrying in acetone, filtering, washing with diethyl ether and drying in vacuo at 60° C. to give the title compound as a colourless solid (99.0 g, 90%). Rf 0.41 (0.880 aqueous ammonia:methanol:dichloromethane 2:14:84, v/v). MS m/z 214 (MH)+. Found: C,47.50; H,8.10; N,16.55; C10H19N3O2 HCl 0.2H2O requires C, 47.41; H, 8.12; N,16.59%.

Workup

  1. customat 0° C.
  2. customwas evaporated under reduced pressure
  3. customto give
  4. filtrationafter filtration
  5. customThis was further purified
  6. filtrationfiltering
  7. washwashing with diethyl ether
  8. customdrying in vacuo at 60° C.

Sources & evidence

ORD record
ord-b3a90ba4b9bf48e3b49e99400775d845
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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