N-Benzylnormechlorethamine → 1-Benzyl-4-(5-fluoro-2,3-dihydro-benzofuran-7-yl)-piperazine

HRID 992043Notes

Reaction equation

HRID 992043 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.Cl[CH2:13][CH2:14][N:15]([CH2:23][CH2:24]Cl)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)CCC>[CH2:16]([N:15]1[CH2:23][CH2:24][N:11]([C:4]2[C:5]3[O:9][CH2:8][CH2:7][C:6]=3[CH:10]=[C:2]([F:1])[CH:3]=2)[CH2:13][CH2:14]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 5928N-BenzylnormechlorethamineHCID 184141795-Fluoro-2,3-dihydrobenzofuran-7-amine

Product 1

HCID 184141301-Benzyl-4-(5-fluoro-2,3-dihydro-benzofuran-7-yl)-piperazineYield 73.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-fluoro-7-amino-2,3-dihydrobenzofuran (1.38 g, 9 mmol) and bis(2-chloroethyl)-benzylamine (3.14 g, 14 mmol) in butanol (20 ml) was stirred at 100° C. for 10 hours. The salt was filtered off, washed with ethyl ether (30 ml) and dried under vacuum: mp 232-233.5° C. The salt was converted to the free base to afford 2.06 g (73%) of the title compound.

Workup

  1. filtrationThe salt was filtered off
  2. washwashed with ethyl ether (30 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-bcf0620cc637424683f5ff143ba39089
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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