HCID 69652458, compound → HCID 69652439, compound

HRID 1058589Notes

Reaction equation

HRID 1058589 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])(C)(C)C>Cl>[NH2:7][C@H:8]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:15][CH2:16]1)=[O:10]

Participants

3

Reactant 1

HCID 69652458HCID 69652458, compound

Product 1

HCID 69652439HCID 69652439, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2.75 g (6.20 mmol) of the above-described (R)-{1-Cyclohexylmethyl-2-[4-(2-methoxyphenyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester was stirred overnight in a mixture of 30 mL of peroxide-free dioxane and 30 mL of 6N aq. HCl. The resulting yellow mixture was concentrated to dryness on a rotary evaporator and the residue was partitioned between dichloromethane and saturated aq. sodium bicarbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to yield the desired (R)-2-amino-3-cyclohexyl-1-[4-(2-methoxyphenyl)-piperazin-1-yl]-propan-1-one (2.10 g, 98% yield), which was characterized as its dihydrochloride salt by conversion with ethereal HCl to yield the white solid; mp=165-168° C.; MS (+) ESI m/z=346 (M+H)+.

Workup

  1. concentrationThe resulting yellow mixture was concentrated to dryness on a rotary evaporator
  2. customthe residue was partitioned between dichloromethane and saturated aq. sodium bicarbonate solution
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-243a8cc6e5974f3690cb6062730f2bbb
Source dataset
uspto-grants-2003_02
Patent number
US06518272B2

Reaction notes

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