Chloroacetonitrile → HCID 22662746, compound

HRID 392066Notes

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 (4piperidinyl)-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-9da30b08dc4f4cabadfcd75c64ce3ade
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800628B2

Reaction notes

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