1-Benzylpiperazine → HCID 58955121, compound

HRID 1990974Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH2:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[C:17]3[S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])(=O)=O)=CC=1.[CH2:32]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[CH2:32]([N:39]1[CH2:44][CH2:43][N:42]([CH2:12][CH2:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[C:17]3[S:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)(=[O:24])=[O:25])[CH2:41][CH2:40]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

Conditions

Temperature: 71 °C

Procedure

A solution of 2-[3-(phenylsulfonyl)-1H-indol-5-yl]ethyl 4-methylbenzenesulfonate (0.16 g, 0.25 mmol) in anhydrous THF (2.5 mL) was added an excess of benzyl piperazine (0.18 mL, 1.02 mmol) and heated to 71° C. for 24 hours. The mixture was partitioned between ethyl acetate and H2O, and the aqueous layer was extracted with ethyl acetate (10 mL). The combined organic layers were washed with 2 M NaOH, (2×15 mL), brine, dried (MgSO4), filtered and concentrated under reduced pressure. Silica gel chromatography (10% EtOH/2N ammonia/dichloromethane) gave the title compound as a light yellow solid (0.11 g, 94%). Mp: 150-153° C. MS (ES+): 460 (M+H).

Workup

customThe mixture was partitioned between ethyl acetate and H2O
extractionthe aqueous layer was extracted with ethyl acetate (10 mL)
washThe combined organic layers were washed with 2 M NaOH, (2×15 mL), brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0f0f57bd03b949e7b5ffffc63b6d1570
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645752B2

Reaction notes

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