Water → HCID 19065937, compound

HRID 481340Notes

Reaction equation

C(N(CC)CC)C.Cl.CN(CCO[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21](Cl)[CH:22]=2)[N:17](C2C=CC(F)=CC=2)[C:16]=1[CH2:32]O)C.CS([Cl:38])(=O)=O.O>ClCCl>[Cl:38][CH2:32][C:16]1[NH:17][C:18]2[C:23]([CH:15]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

Conditions

Temperature: -10 °C

Procedure

Triethylamine (1 g) was added to a solution of N,N-dimethyl-2-[5-chloro-1-(4-fluorophenyl)-2-hydroxymethyl-3-1H-indolyloxy]ethylamine 9 (3 g) in dichloromethane (100 mL) cooled to -10° C. A solution of methanesulfonylchloride (1.1 g) in dichloromethane (25 mL) was added dropwise at -10° to 0° C. After stirring for 1/2 h at 0° C. ice cooled water was added and the organic phase was subsequently worked up leaving the 2-chloromethylindole derivative as an oil. This oil was used immediately without further purification. To a solution of the oil in dry THF was added LiAlH4 (1 g). After refluxing for 1 h, the mixture was cooled on an ice bath and excess LiAlH4 was hydrolyzed by cautiously adding a mixture of 10% water in THF. Inorganic salts were filtered off and the solvent evaporated in vacuo . The resulting visceous oil was subjected to column chromatography on silica gel (eluted with 4% triethylamine in ethyl acetate) yielding the pure title compound as an oil. Yield: 0.6 g. The oxalic acid salt 10 crystallized from 2-propanol. mp 236°-237° C.; 1H NMR (DMSO-d6) δ 2.15 (s, 3H), 2.85 (s, 6H), 3.40 (t, 2H), 4.35 (t, 2H), 7.00 (d, 1H), 7.05 (dd, 1H), 7.40 (t, 2H), 7.45 (dd, 2H), 7.70 (d, 1H). MS (m/z) 347 (MH+), 274 (6), 223 (36), 222 (20), 72 (100); Anal (C19H20ClFN2O.C2H2O4) C, H, N.

Workup

additionwas added

Sources & evidence

ORD record: ord-324619e0312f45fab9bba80dae57df90
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05789404

Reaction notes

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