Chloroacetonitrile → HCID 22662746, compound

HRID 1596390Notes

Reaction equation

Cl[CH2:2][C:3]#[N:4].[NH2:5][C:6]1[C:11]2[O:12][CH2:13][CH2:14][O:15][C:10]=2[C:9]([C:16]([O:18][CH2:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:17])=[CH:8][C:7]=1[Cl:26]>C(N(CC)CC)C.CN(C=O)C>[NH2:5][C:6]1[C:11]2[O:12][CH2:13][CH2:14][O:15][C:10]=2[C:9]([C:16]([O:18][CH2:19][CH:20]2[CH2:21][CH2:22][N:23]([CH2:2][C:3]#[N:4])[CH2:24][CH2:25]2)=[O:17])=[CH:8][C:7]=1[Cl:26]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of chloroacetonitrile (2.15 ml) and (4-piperidinyl)-methyl 8-amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-carboxylate (11 g) in N,N-diethylethanamine (7 ml) and DMF (150 ml) was stirred at 60° C. until the reaction was complete. Then, the mixture was cooled. The solvent was evaporated. The residue was partitioned between DCM and water. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was crystallized from ACN and the precipitate was filtered off and dried (vacuum, 50° C.), yielding 6.6 g (53%) [1-(cyanomethyl)-4-piperidinyl]-methyl 8-amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-carboxylate (intermediate 14).

Workup

temperatureThen, the mixture was cooled
customThe solvent was evaporated
customThe residue was partitioned between DCM and water
customThe separated organic layer was dried
filtrationfiltered
customthe solvent was evaporated
customThe residue was crystallized from ACN
filtrationthe precipitate was filtered off
customdried (vacuum, 50° C.)

Sources & evidence

ORD record: ord-5948a0a7a63b487b8bd0569f28fd6ea7
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291481B1

Reaction notes

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