Hydrochloric Acid → 4-{4-[(7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-butyl}-[1,4]diazepan-5-one

HRID 2415230Notes

Reaction equation

HRID 2415230 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]([CH:24]2[CH2:33][CH2:32][C:31]3[C:26](=[CH:27][C:28]([O:34][CH3:35])=[CH:29][CH:30]=3)[CH2:25]2)[CH2:21][CH2:22][CH3:23])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.Cl>C(Cl)Cl.C(OCC)C>[CH3:35][O:34][C:28]1[CH:27]=[C:26]2[C:31]([CH2:32][CH2:33][CH:24]([N:20]([CH2:21][CH2:22][CH3:23])[CH2:19][CH2:18][CH2:17][CH2:16][N:11]3[C:12](=[O:15])[CH2:13][CH2:14][NH:8][CH2:9][CH2:10]3)[CH2:25]2)=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 11352263HCID 11352263, compound

Product 1

HCID 102218334-{4-[(7-Methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-butyl}-[1,4]diazepan-5-oneYield 115.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To 4-{4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (800 mg, 1.64 mmol) in methylene chloride (15 mL) was added trifluoroacetic acid (5 mL) in a single portion and the reaction was stirred at room temperature for 30 min. The mixture was concentrated to dryness in-vacuo, dissolved in water (40 mL) and treated with 15% aq. KOH (20 mL). The solution was extracted with ethyl acetate, washed with brine, dried (MgSO4) and concentrated in-vacuo. The free base (636 mg, 1.64 mmol) was taken up in diethyl ether (30 mL) and treated with 1M HCl in ether (3.3 mL). The solid was collected and dried under vacuum to afford 732 mg of 4-{4-[(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-butyl}-[1,4]diazepan-5-one 5 as a dihydrochloride salt. MS: 374([M+H]+).

Workup

  1. concentrationThe mixture was concentrated to dryness in-vacuo
  2. dissolutiondissolved in water (40 mL)
  3. additiontreated with 15% aq. KOH (20 mL)
  4. extractionThe solution was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in-vacuo
  8. customThe solid was collected
  9. customdried under vacuum

Sources & evidence

ORD record
ord-c19e02f4971f43acbb3b8064441c15d1
Source dataset
uspto-grants-2004_11
Patent number
US06818645B2

Reaction notes

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